The present invention relates to condensed heterocyclic compounds and their use.
The present inventors have extensively studied to find compounds having excellent herbicidal activity. As a result, they have found that the condensed heterocyclic compounds of general formula I as depicted below have excellent herbicidal activity, thereby completing the present invention.
The present invention provides condensed heterocyclic compounds of general formula I: 
(hereinafter referred to as the present compounds)
wherein T is carbon or nitrogen; when T is carbon, then the bond between T and A is a double bond, the bond between A and Y is a single bond, and Y is oxygen, sulfur, or Nxe2x80x94R142; or when T is nitrogen, then the bond between T and A is a single bond, the bond between A and Y is a double bond, and Y is nitrogen or Cxe2x80x94R152;
wherein R142 is hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, cyano, xe2x80x94COR143, xe2x80x94N(R145)R146, or xe2x80x94Nxe2x95x90C(R147)R148; R152 is hydrogen, halogen, C1-C3 alkyl, nitro, amino, cyano, or xe2x80x94COR153;
xe2x80x83wherein R143 is hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, hydroxyl, C1-C5 alkoxy, or xe2x80x94N(R156)N157; R145 and R146 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, formyl, (C1-C5 alkyl)carbonyl, (C1-C5 haloalkyl)carbonyl, or (C1-C6 alkoxy)carbonyl; R147 and R148 are independently hydrogen or C1-C5 alkyl; R153 is hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, hydroxyl, C1-C5 alkoxy, or xe2x80x94N(R154)R155;
wherein R156 and R157 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, formyl, (C1-C5 alkyl)carbonyl, (C1-C5 haloalkyl)carbonyl, or (C1-C5 alkoxy)carbonyl; R154 and R155 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, (C1-C5 alkoxy)carbonyl, formyl, (C1-C5 alkyl)carbonyl, or (C1-C5 haloalkyl)carbonyl;
A is nitrogen or Cxe2x80x94R141 wherein R141 is hydrogen, halogen, or C1-C3 alkyl;
R1 is hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, hydroxymethyl, nitro, or cyano;
R2 is hydrogen, halogen, C1-C11 alkyl, C1-C11 haloalkyl, hydroxymethyl, nitro, cyano, xe2x80x94N(R9)R10, xe2x80x94OR11, xe2x80x94SR12, xe2x80x94SO2R13, xe2x80x94COX, xe2x80x94COOR14, xe2x80x94CON(R15)R16, xe2x80x94COR17, xe2x80x94C(R26)xe2x95x90NOR19, xe2x80x94C(R27)xe2x95x90C(R21)R22, or xe2x80x94CH(R23)xe2x80x94CH(R24)R25;
R3 is hydrogen, halogen, C1-C11 alkyl, C1-C11 haloalkyl, hydroxymethyl, nitro, cyano, xe2x80x94N(R59)R60, xe2x80x94OR61, xe2x80x94SR62, xe2x80x94SO2R63, xe2x80x94COX, xe2x80x94COOR64, xe2x80x94CON(R65)R66, xe2x80x94COR67, xe2x80x94C(R76)xe2x95x90NOR69, xe2x80x94C(R77)xe2x95x90C(R71)R72, or xe2x80x94CH(R73)xe2x80x94CH(R74)R75;
R4 is hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, hydroxymethyl, nitro, or cyano;
xe2x80x83wherein X is chlorine or bromine;
R9 and R59 are independently hydrogen, C1-C5 alkyl, (C1-C5 alkyl)carbonyl, or (C1-C5 alkoxy)carbonyl;
R10, R11, and R12 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, cyano C1-C6 alkyl, (C1-C5 alkyl)carbonyl, (C1-C5 haloalkyl)carbonyl, (C3-C10 cycloalkyl)carbonyl, (C1-C5 alkyl)carbonyl, C1-C5 alkyl, (C1-C5 haloalkyl)carbonyl C1-C5 alkyl, hydroxy C1-C5 alkyl, C1-C5 alkoxy C1-C5 alkyl, C1-C5 alkylthio C1-C5 alkyl, (C1-C5 alkoxy)carbonyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, xe2x80x94C(R43)(R44)xe2x80x94C(xe2x95x90O)ON(R45)R46, xe2x80x94C(R47)(R48) xe2x80x94CON(R49)R50, xe2x80x94CH2xe2x80x94C(R56)xe2x95x90NOR55, xe2x80x94CHMexe2x80x94C(R58)xe2x95x90NOR57, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, carboxy(C1-C5 alkyl)carbonyl, (C1-C10 alkoxy)carbonyl(C1-C5 alkyl)carbonyl, (C1-C10 haloalkoxy)carbonyl(C1-C5 alkyl)carbonyl, C1-C5 alkylsulfonyl, C1-C5 haloalkylsulfonyl, xe2x80x94SO2N(R51)R52, xe2x80x94CON(R53)R54, optionally substituted benzyl, or optionally substituted phenyl;
R60, R61, and R62 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, cyano C1-C6 alkyl, (C1-C5 alkyl)carbonyl, (C1-C5 haloalkyl)carbonyl, (C3-C10 cycloalkyl)carbonyl, (C1-C5 alkyl)carbonyl C1-C5 alkyl, (C1-C5 haloalkyl)carbonyl C1-C5 alkyl, hydroxy C1-C5 alkyl, C1-C5 alkoxy C1-C5 alkyl, C1-C5 alkylthio C1-C5 alkyl, (C1-C5 alkoxy)carbonyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C10 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, xe2x80x94C(R163)(R164)xe2x80x94C(xe2x95x90O)ON(R165)R166, xe2x80x94C(R167)R168)xe2x80x94CON(R169)R170, xe2x80x94CH2xe2x80x94C(xe2x95x90NOR175)R176, xe2x80x94CHMexe2x80x94C(xe2x95x90NOR177)R178, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, carboxy(C1-C5 alkyl)carbonyl, (C1-C110 alkoxy)carbonyl(C1-C5 alkyl)carbonyl, (C1-C10 haloalkoxy)carbonyl(C1-C5 alkyl)carbonyl, C1-C5 alkylsulfonyl, C1-C5 haloalkylsulfonyl, xe2x80x94SO2N(R171)R172, xe2x80x94CON(R173)R174, optionally substituted benzyl, or optionally substituted phenyl;
xe2x80x83wherein R43, R44, R163, and R164 are independently hydrogen, halogen, C1-C5 alkyl, or C1-C5 haloalkyl;
R45, R46, R165, and R166 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R45 and R46 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring, or R165 and R166 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;
R47, R48, R167, and R168 are independently hydrogen, halogen, C1-C5 alkyl, or C1-C5 haloalkyl;
R49, R50, R169, and R170 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R49 and R50 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R169 and R170 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
R51, R52, R171, and R172 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R51 and R52 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R171 and R172 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
R53, R54, R173, and R174 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R53 and R54 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R173 and R174 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated, ring containing zero to one oxygen atom or NH group in the ring;
R55, R57, R175, and R177 are independently hydrogen or C1-C3 alkyl;
R56, R58, R176, and R178 are independently hydrogen, C1-C5 alkyl, (C1-C5 alkoxy)carbonyl, (C1-C5 haloalkoxy)carbonyl, (C3-C5 cycloalkoxy)carbonyl, (C3-C5 alkenoxy)carbonyl, or (C3-C5 alkynoxy)carbonyl;
R13 is hydroxy, chlorine, C1-C10 alkyl, C1-C10 haloalkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, xe2x80x94N(R79)R80, or xe2x80x94OR81;
R63 hydroxy, chlorine, C1-C10 alkyl, C1-C10 haloalkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, xe2x80x94N(R179)R180, or xe2x80x94OR181;
xe2x80x83wherein R79 and R179 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl; R80 and R180 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R79 and R80 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- or 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R179 and R180 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- or 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; and R81 and R181 are independently C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
R14 is hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, xe2x80x94N(R82)R83, optionally substituted benzyl, or optionally substituted phenyl;
R64 is hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, xe2x80x94N(R182)R183, optionally substituted benzyl, or optionally substituted phenyl;
xe2x80x83wherein R82 and R182 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl; R83 and R183 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R82 and R83 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R182 and R183 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
R15 and R65 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 alkynyl, cyano C1-C6 alkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, optionally substituted benzyl, or optionally substituted phenyl; R16 and R66 are independently hydrogen, C1-C10 alkyl, or C1-C10 haloalkyl; or R15 and R16 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R65 and R66 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
R17, R26, R27, R67, R76, and R77 are independently hydrogen, cyano, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, (C1-C6 alkoxy)carbonyl, or (C1-C6 alkoxy)carbonylmethyl;
R19 and R69 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, cyano C1-C6 alkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
R21 and R71 are independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
R22 and R25 are independently carboxy, (C1-C10 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl, (C3-C10 halocycloalkoxy)carbonyl, carboxy(C1-C5 alkoxy)carbonyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkenoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkynoxy)carbonyl (C1-C5 alkoxy)carbonyl, xe2x80x94CON(R84)R85, or xe2x80x94C(xe2x95x90O)ON(R86)R87;
R72 and R75 are independently carboxy, (C1-C10 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl, (C3-C10 halocycloalkoxy)carbonyl, carboxy(C1-C5 alkoxy)carbonyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkenoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkynoxy)carbonyl (C1-C5 alkoxy)carbonyl, xe2x80x94CON(R184R185, or xe2x80x94C(xe2x95x90O)ON(R186)R187;
xe2x80x83wherein R84 and R184 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl; R85 and R185 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R84 and R85 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring; or R184 and R185 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
R86 and R186 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl; R87 and R187 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl; or R86 and R87 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring; or R186 and R187 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;
R23, R24, R73, and R74 are independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl; and
Q is any one group of Q1 to Q23 of the general formula: 
xe2x80x83wherein:
in Q1, E1 and E2 are independently C1-C6 alkyl optionally substituted with halogen, or C3-C6 cycloalkyl optionally substituted with halogen; or E1 and E2 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen;
in Q2, E3 and E4 are independently C1-C6 alkyl optionally substituted with halogen, or C3-C6 cycloalkyl optionally substituted with halogen; or E3 and E4 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen; D1 and D2 are independently oxygen or sulfur; and Z1 is nitrogen or CH;
in Q3, E5 is hydrogen or C1-C6 alkyl optionally substituted with halogen; and D3 is oxygen or sulfur;
in Q4, E6 and E7 are independently hydrogen, C1-C6 alkyl optionally substituted with halogen, or C3-C6 cycloalkyl optionally substituted with halogen; or E6 and E7 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen;
in Q5, E8 and E9 are independently hydrogen, C1-C6 alkyl optionally substituted with halogen, or C3-C6 cycloalkyl optionally substituted with halogen; or E8 and E9 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen;
in Q6, E10 is hydrogen, C1-C6 alkyl optionally substituted with halogen, or C1-C3 alkoxy optionally substituted with halogen; E11 is hydrogen or C1-C6 alkyl optionally substituted with halogen; or E10 and E11 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen; and E44 is halogen or C1-C3 alkyl;
in Q7, E12 is C1-C6 alkyl optionally substituted with halogen; and D4 is oxygen or sulfur;
in Q8, E13 is C1-C6 alkyl optionally substituted with halogen; and E14 is hydrogen or halogen;
in Q9, E15 is hydrogen or C1-C6 alkyl; E16 is C1-C6 alkyl optionally substituted with halogen; or E15 and E16 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen;
in Q10, E17, E18, and E19 are independently hydrogen or C1-C6 alkyl; and D5 is oxygen or sulfur;
in Q11, E20 and E21 are independently hydrogen or C1-C6 alkyl; and D6 is oxygen or sulfur;
in Q12, E22 and E23 are independently hydrogen or C1-C6 alkyl;
in Q13, E24 is hydrogen or C1-C3 alkyl;
in Q14, E25 is hydrogen, C1-C3 alkyl, or halogen; E26 is C1-C3 alkyl optionally substituted with halogen; E27 is hydrogen, amino, C1-6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, or optionally substituted benzyl; and D7 is oxygen or sulfur;
in Q15, E28 is C1-C3 alkyl optionally substituted with halogen; E29 is hydrogen, amino, C1-C6 alkyl, C1-C6 alkenyl, C3-C6 alkynyl, or optionally substituted benzyl; and D8 is oxygen or sulfur;
in Q16, E30 is C1-C3 alkyl optionally substituted with halogen, E31 is hydrogen or C1-C3 alkyl optionally substituted with halogen; or E30 and E31 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring (which unsaturated ring includes no aromatic rings), and the ring may optionally be substituted with methyl or halogen; and E42 is hydrogen or C1-C3 alkyl optionally substituted with halogen;
in Q17, E32 is C1-C3 alkyl optionally substituted with halogen; E33 is hydrogen, halogen, amino, C1-C3 alkyl optionally substituted with halogen, C1-C3 alkoxy optionally substituted with halogen, or C1-C3 alkylthio optionally substituted with halogen; and E43 is hydrogen or C1-C3 alkyl optionally substituted with halogen;
in Q18, E34 is C1-C3 alkyl optionally substituted with halogen;
in Q19, D9 is oxygen or sulfur; and V1 is xe2x80x94CH2xe2x80x94, xe2x80x94CH2xe2x80x94CH2xe2x80x94, or xe2x80x94CH2xe2x80x94CH2xe2x80x94CH2xe2x80x94;
in Q20, E35 is C1-C3 alkyl optionally substituted with halogen; Z2 is nitrogen or CH; and V2 is xe2x80x94CH2xe2x80x94CH2xe2x80x94, xe2x80x94CHxe2x95x90CHxe2x80x94, xe2x80x94Nxe2x95x90CHxe2x80x94, xe2x80x94CHxe2x95x90Nxe2x80x94, or xe2x80x94Nxe2x95x90Nxe2x80x94;
in Q21, E36 and E37 are independently C1-C6 alkyl; or E36 and E37 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen; D10 and D11 are independently oxygen or sulfur; and Z3 is nitrogen or CH;
in Q22, E38 is hydrogen or C1-C6 alkyl; E39 is C1-C3 alkyl optionally substituted with halogen; or E38 and E39 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen; and D12 is oxygen or sulfur; and
in Q23, E40 is hydrogen or C1-C6 alkyl; E41 is C1-C3 alkyl, or C3-C6 cycloalkyl; or E40 and E41 may be combined at their ends to form, together with the atoms attached thereto, a 4- to 7-membered saturated or unsaturated ring containing zero to two O, S, SO, SO2, or NH groups in the ring, and the ring may optionally be substituted with methyl or halogen; and D13 is oxygen or sulfur.
The present invention further provides herbicides containing them as active ingredients, and condensed heterocyclic compounds of general formula II: 
wherein A1 is Cxe2x80x94R31 and Y11 is oxygen, sulfur, or Nxe2x80x94R32; wherein R31 is nitro, amino, cyano, carboxyl, or (C1-C3 alkoxy)carbonyl, and R32 is hydrogen, C1-C5 alkyl, C3-C6 alkenyl, or C3-C6 alkynyl; and Q, R1, R2, R3, and R4 are as defined above, which heterocyclic compounds are useful as intermediates for the production of the present compounds.
For the groups represented by R142, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
For the groups-represented by R143, C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl; C1-C3 haloalkyl may include trifluoromethyl and difluoromethyl; and C1-C5 alkoxy may include methoxy, ethoxy, propoxy, and isopropoxy.
For the groups represented by R145 or R146, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; (C1-C5 alkyl)carbonyl may include acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, and butylcarbonyl; (C1-C5 haloalkyl)carbonyl may include trifluoroacetyl, difluoroacetyl, chlorodifluoroacetyl, and dichloroacetyl; and (C1-C5 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, and isopropoxycarbonyl.
For the groups represented by R147 or R148, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl.
For the elements or groups represented by R152, halogen may include fluorine, chlorine, bromine, and iodine; and C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl.
For the groups represented by R153, C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl; C1-C3 haloalkyl may include trifluoromethyl and difluoromethyl; and C1-C5 alkoxy may include methoxy, ethoxy, propoxy, and isopropoxy.
For the groups represented by R156 or R157, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; (C1-C5 alkyl)carbonyl may include acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, and butylcarbonyl; (C1-C5 haloalkyl)carbonyl may include trifluoroacetyl, difluoroacetyl, chlorodifluoroacetyl, and dichloroacetyl; and (C1-C5 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, and isopropoxycarbonyl.
For the groups represented by R154 or R155, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; (C1-C5 alkyl)carbonyl may include acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, and butylcarbonyl; (C1-C5 haloalkyl)carbonyl may include trifluoroacetyl, difluoroacetyl, chlorodifluoroacetyl, and dichloroacetyl; and (C1-C5 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, and isopropoxycarbonyl.
For the groups or elements represented by R141, C1-C3 alkyl may include methyl, ethyl, and isopropyl; and halogen may include fluorine, chlorine, bromine, and iodine.
For groups represented by R31, (C1-C3 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and isopropoxycarbonyl.
For the groups represented by R32, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
For the elements or groups represented by R1, halogen may include fluorine, chlorine, bromine, and iodine; C1-C3 alkyl may include methyl and ethyl; and C1-C3 haloalkyl may include trifluoromethyl and difluoromethyl.
For the elements or groups represented by R2 or R3, halogen may include fluorine, chlorine, bromine, and iodine; C1-C11 alkyl may include methyl, ethyl, and isopropyl; and C1-C11 haloalkyl may include trichloromethyl, trifluoromethyl, chlorodifluoromethyl, difluoromethyl, pentafluoroethyl, and 1,1-difluoroethyl.
For the elements or groups represented by R4, halogen may include fluorine, chlorine, bromine, and iodine; C1-C3 alkyl may include methyl and ethyl; and C1-C3 haloalkyl may include trifluoromethyl and difluoromethyl.
For the groups represented by R9 or R59, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl (wherein xe2x80x9ctxe2x80x9d means xe2x80x9ctertiaryxe2x80x9d; this also holds below), and isoamyl; (C1-C5 alkyl)carbonyl may include acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, and butylcarbonyl; and (C1-C5 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, and t-butoxycarbonyl.
For the groups represented by R10, R11, R12, R60, R61, or R62, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, isoamyl, pentyl, hexyl, heptyl, and octyl; C1-C10 haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and 2,2,2-trifluoroethyl; C3-C10 cycloalkyl may include cyclopentyl and cyclohexyl; C1-C10 halocycloalkyl may include 4,4,-difluorocyclopentyl and 3-chlorocyclohexyl; C3-C10 cycloalkyl C1-C3 alkyl may include cyclopropylmethyl, cyclopentylmethyl, and cyclohexylmethyl; C3-C10 alkenyl may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C3-C10 haloalkenyl may include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl; C3-C10 alkynyl may include propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, and 1,1-dimethyl-2-propynyl; C3-C10 haloalkynyl may include 3-iodo-2-propynyl and 3-bromo-2-propynyl; cyano C1-C6 alkyl may include cyanomethyl and cyanoethyl; (C1-C5 alkyl)carbonyl may include acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, and butylcarbonyl; (C1-C5 haloalkyl)carbonyl may include trifluoroacetyl, difluoroacetyl, chlorodifluoroacetyl, and dichloroacetyl; (C3-C10 cycloalkyl)carbonyl may include cyclopropylcarbonyl and cyclopentylcarbonyl; (C1-C5 alkyl)carbonyl C1-C5 alkyl may include 2-oxopropyl, 3-methyl-2-oxobutyl, and 3-oxopentyl; (C1-C5 haloalkyl)carbonyl C1-C5 alkyl may include 3,3,3-trifluoro-2-oxopropyl; hydroxy C1-C5 alkyl may include 2-hydroxyethyl and 4-hydroxybutyl; C1-C5 alkoxy C1-C5 alkyl may include methoxymethyl, 1-methoxyethyl, and ethoxymethyl; C1-C5 alkylthio C1-C5 alkyl may include methylthiomethyl and methylthioethyl; (C1-C5 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, and t-butoxycarbonyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl; (C3-C10 alkenoxy)carbonyl C1-C5 alkyl may include allyoxycarbonylmethyl, 1-methyl-2-propenyloxycarbonylmethyl, 1-allyloxycarbonylethyl, and 1-(1-methyl-2-propenyloxy)carbonylethyl; (C3-C10 alkynoxy)carbonyl C1-C5 alkyl may include propargyloxycarbonylmethyl, 1-methyl-2-propynyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 1-(1-methyl-2-propynyloxy)carbonylethyl; carboxy(C1-C5 alkoxy)carbonyl C1-C5 alkyl may include carboxymethoxycarbonylmethyl, 1-carboxyethoxycarbonylmethyl, 1-carboxy-1-methylethoxycarbonylmethyl, 1-(carboxymethoxycarbonyl)ethyl, 1-(1-carboxyethoxycarbonyl)ethyl, and 1-(1-carboxy-1-methylethoxy-carbonyl)ethyl; (C1-C10 alkoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethoxycarbonylmethyl, 1-methoxycarbonylethoxycarbonylmethyl, 1-methoxycarbonyl-1-methylethoxycarbonylmethyl, 1-(methoxycarbonylmethoxycarbonyl)ethyl, 1-(1-methoxycarbonylethoxycarbonyl)ethyl, 1-(1-methoxycarbonyl-1-methylethoxycarbonyl)ethyl, ethoxycarbonylmethoxycarbonylmethyl, 1-ethoxycarbonylethoxycarbonylmethyl, 1-ethoxycarbonyl-1-methylethoxycarbonylmethyl, 1-(ethoxycarbonylmethoxycarbonyl)ethyl, 1-(1-ethoxycarbonylethoxycarbonyl)ethyl, 1-(1-ethoxycarbonyl-1-methylethoxycarbonyl)ethyl, isopropoxycarbonylmethoxy-carbonylmethyl, 1-isopropoxycarbonylethoxycarbonylmethyl, 1-isopropoxycarbonyl-1-methylethoxycarbonylmethyl, 1-(isopropoxycarbonylmethoxycarbonyl)ethyl, 1-(1-isopropoxycarbonylethoxycarbonyl)ethyl, and 1-(1-isopropoxycarbonyl-1-methylethoxycarbonyl)ethyl; (C1-C10 haloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethoxycarbonylmethyl, 1-(2-chloroethoxycarbonyl)ethoxycarbonylmethyl, 1-(2-chloroethoxycarbonyl)-1-methylethoxycarbonylmethyl, 1-(2-chloroethoxycarbonylmethoxycarbonyl)ethyl, 1-{1-(2-chloroethoxycarbonyl)ethoxycarbonyl}ethyl, and 1-{1-(2-chloroethoxycarbonyl)-1-methylethoxycarbonyl}-ethyl; (C3-C10 cycloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethoxycarbonylmethyl, 1-cyclopentyloxycarbonylethoxycarbonylmethyl, 1-cyclopentyloxycarbonyl-1-methylethoxycarbonylmethyl, 1-(cyclopentyloxycarbonylmethoxycarbonyl)ethyl, 1-(1-cyclopentyloxycarbonylethoxycarbonyl)ethyl, 1-(1-cyclopentyloxycarbonyl-1-methylethoxycarbonyl)ethyl, cyclohexyloxycarbonylmethoxycarbonylmethyl, 1-cyclohexyloxycarbonylethoxycarbonylmethyl, 1-cyclohexyloxycarbonyl-1-ethylethoxycarbonylmethyl, 1-(cyclohexyloxycarbonylmethoxycarbonyl)ethyl, 1-(1-cyclohexyloxycarbonylethoxycarbonyl)ethyl, and 1-(1-cyclohexyloxycarbonyl-1-methylethoxycarbonyl)ethyl; (C3-C10 alkenoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl may include allyloxycarbonylmethoxycarbonylmethyl, 1-allyloxycarbonylethoxycarbonylmethyl, 1-allyloxycarbonyl-1-methylethoxycarbonylmethyl, 1-(allyloxycarbonylmethoxycarbonyl)ethyl, 1-(1-allyloxycarbonylethoxycarbonyl)ethyl, and 1-(1-allyloxycarbonyl-1-methylethoxycarbonyl)ethyl; (C3-C10 alkynoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl may include propargyloxycarbonylmethoxycarbonylmethyl, 1-propargyloxycarbonylethoxycarbonylmethyl, 1-propargyloxycarbonyl-1-methylethoxycarbonylmethyl, 1-(propargyloxycarbonylmethoxycarbonyl)ethyl, 1-(1-propargyloxycarbonylethoxycarbonyl)ethyl, and 1-(1-propargyloxycarbonyl-1-methylethoxycarbonyl)ethyl; carboxy(C1-C5 alkyl)carbonyl may include carboxymethylcarbonyl, carboxyethylcarbonyl, 1-carboxy-1-methylethylcarbonyl, 2-carboxyethylcarbonyl, 3-carboxypropylcarbonyl, and 3-carboxy-1-methylpropylcarbonyl; (C1-C10 alkoxy)carbonyl(C1-C5 alkyl)carbonyl may include methoxycarbonylmethylcarbonyl, 1-methoxycarbonylethylcarbonyl, 1-methoxycarbonyl-1-methylethylcarbonyl, 2-methoxycarbonylethylcarbonyl, 3-methoxycarbonylpropylcarbonyl, 3-methoxycarbonyl-1-methylpropylcarbonyl, ethoxycarbonylmethylcarbonyl, 1-ethoxycarbonylethylcarbonyl, 1-ethoxycarbonyl-1-methylethylcarbonyl, 2-ethoxycarbonylethylcarbonyl, 3-ethoxycarbonylpropylcarbonyl, and 3-ethoxycarbonyl-1-methylpropylcarbonyl; (C1-C10 haloalkoxy)carbonyl(C1-C5 alkyl)carbonyl may include 2-chloroethoxycarbonylmethylcarbonyl, 2,2,2-trifluoroethoxycarbonylmethylcarbonyl, 3-bromopropoxycarbonylmethylcarbonyl, 1-(2-chloroethoxy)carbonylethylcarbonyl, and 1-(2,2,2-trifluoroethoxy)carbonylethylcarbonyl; C1-C5 alkylsulfonyl may include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, and butylsulfonyl; C1-C5 haloalkylsulfonyl may include chloromethylsulfonyl, and trifluoromethylsulfonyl; optionally substituted benzyl may include benzyl; and optionally substituted phenyl may include phenyl.
For the groups represented by R13 or R63, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, and isoamyl; C1-C10 haloalkyl may include trifluoromethyl; carboxy C1-C5 alkyl may include carboxymethyl, carboxyethyl, 1-carboxyethyl, and 2-carboxypropyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxyvcarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclo hexyloxycarbonylmethyl.
For the groups represented by R14 or R64, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, isoamyl, pentyl, hexyl, heptyl, and octyl; C1-C10 haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and 2,2,2-trifluoroethyl; C3-C10 cycloalkyl may include cyclopentyl and cyclohexyl; C3-C10 halocycloalkyl may include 4,4,-difluorocyclopentyl and 3-chlorocyclohexyl; C3-C10 cycloalkyl C1-C3 alkyl may include cyclopropylmethyl, cyclopentylmethyl, and cyclohexylmethyl; C3-C10 alkenyl may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C3-C10 haloalkenyl may include 2-chloro-2-propenyl, and 3,3-dichloro-2-propenyl; C3-C10 alkynyl may include propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, and 1,1-dimethyl-2-propynyl; C3-C10 haloalkynyl may include 3-iodo-2-propynyl, and 3-bromo-2-propynyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, 2-carboxyethyl, and 1-carboxy-1-methylethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonyl methyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-methoxycarbonyl-1-methylethyl, 1-ethoxycarbonyl-1-methylethyl, 1-propoxycarbonyl-1-methylethyl, 1-isopropoxycarbonyl-1-methylethyl, 1-butoxycarbonyl-1-methylethyl, 1-isobutoxycarbonyl-1-methylethyl, 1-t-butoxycarbonyl-1-methylethyl, 1-amyloxycarbonyl-1-methylethyl, 1-isoamyloxycarbonyl-1-methylethyl, and 1-t-butoxycarbonyl-1-methylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, 1-(2,2,2-trifluoroethoxy)carbonylethyl, 1-(2-chloroethoxy)carbonyl-1-methylethyl, and 1-(2,2,2-trifluoroethoxy)carbonyl-1-methylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, 1-cyclohexyloxycarbonylethyl, 1-cyclopentyloxycarbonyl-1-methylethyl, and 1-cyclohexyloxycarbonyl-1-methylethyl; (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl, and 1-(4-fluorocyclohexyloxycarbonyl)-1-methylethyl; (C3-C10 alkenoxy)carbonyl C1-C5 alkyl may include allyloxycarbonylmethyl, 1-methyl-2-propenyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 1-(1-methyl-2-propenyloxy)carbonylethyl, 1-allyloxycarbonyl-1-methylethyl, and 1-(1-methyl-2-propenyloxy)carbonyl-1-methylethyl; (C3-C10 alkynoxy)carbonyl C1-C5 alkyl may include propargyloxycarbonylmethyl, 1-methyl-2-propynyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 1-(1-methyl-2-propynyloxy)carbonylethyl, 1-propargyloxycarbonyl-1-methylethyl, and 1-(1-methyl-2-propynyloxy)carbonyl-1-methylethyl; optionally substituted benzyl may include benzyl; and optionally substituted phenyl may include phenyl.
For the groups represented by R15 or R65, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, isoamyl, pentyl, hexyl, heptyl, and octyl; C1-C10 haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and 2,2,2-trifluoroethyl; C3-C10 cycloalkyl may include cyclopentyl, and cyclohexyl; C3-C10 cycloalkyl C1-C3 alkyl may include cyclopropylmethyl, cyclopentylmethyl, and cyclohexylmethyl; C3-C10 alkenyl may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C3-C10 alkynyl may include propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, and 1,1-dimethyl-2-propynyl; cyano C1-C6 alkyl may include cyanomethyl, and cyanoethyl; carboxyC1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; optionally substituted benzyl may include benzyl; and optionally substituted phenyl may include phenyl.
For the groups represented by R16 or R66, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, isoamyl, pentyl, hexyl, heptyl, and octyl; and C1-C10 haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and 2,2,2-trifluoroethyl.
The 3- to 7-membered saturated ring, which is formed by combining R15 and R16 or R65 and R66 at their ends, together with the adjacent nitrogen atom, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R17, R26, R27, R67, R76, or R77, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, isoamyl, pentyl, hexyl, heptyl, and octyl; C1-C10 haloalkyl may include 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and 2,2,2-trifuoroethyl; C3-C10 cycloalkyl may include cyclopentyl, and cyclohexyl; C3-C10 cycloalkyl C1-C3 alkyl may include cyclopropylmethyl, cyclopentylmethyl, and cyclohexylmethyl; (C1-C6 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and isopro-poxycarbonyl; and (C1-C6 alkoxy)carbonylmethyl may include methoxy carbonylmethyl, ethoxycarbonylmethyl, and isopropoxycarbonylmethyl.
For the groups represented by R19 or R69, C1-C10 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, t-butyl, isoamyl, pentyl, hexyl, heptyl, and octyl; C1-C10 haloalkyl may include 2-fluoroethyl, 2-chloro-ethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and 2,2,2-trifluoroethyl; C3-C10 cycloalkyl may include cyclopentyl and cyclohexyl; C3-C10 halocycloalkyl may include 4,4,-difluorocyclopentyl and 3-chlorocyclohexyl; C3-C10 cycloalkyl C1-C3 alkyl may include cyclopropylmethyl, cyclopentylmethyl, and cyclohexylmethyl; C3-C10 alkenyl may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C3-C10 haloalkenyl may include 2-chloro-2-propenyl, and 3,3-dichloro-2-propenyl; C3-C10 alkynyl may include propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, and 1,1-dimethyl-2-propynyl; C3-C10 haloalkynyl may include 3-iodo-2-propynyl, and 3-bromo-2-propynyl; cyano C1-C6 alkyl may include cyanomethyl and cyanoethyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl.
For the elements or groups represented by R21 or R71, halogen may include fluorine, chlorine, bromine, and iodine; C1-C3 alkyl may include methyl and ethyl; and C1-C3 haloalkyl may include trifluoromethyl.
For the groups represented by R22, R25, R72, or R75, (C1-C10 alkoxy) carbonyl may include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, t-butoxycarbonyl, amyloxycarbonyl, and isoamyloxycarbonyl; (C1-C10 haloalkoxy)carbonyl may include 2-chloroethoxycarbonyl, 2-fluoroethoxycarbonyl, 3-bromopropoxycarbonyl, 3-chlorobutoxycarbonyl, and 5,5-dichloroamyloxycarbonyl; (C3-C10 cycloalkoxy)carbonyl may include cyclopentyloxycarbonyl and cyclohexylcarbonyl; (C3-C10 halocycloalkoxy)carbonyl may include 4,4-difluorocyclohexyloxycarbonyl; carboxy(C1-C5 alkoxy)carbonyl may include carboxymethoxycarbonyl, 1-carboxyethoxycarbonyl, and 1-carboxy-1-methylethoxycarbonyl; (C1-C10 alkoxy)carbonyl(C1-C5 alkoxy)carbonyl may include methoxycarbonylmethoxycarbonyl, 1-methoxycarbonylethoxycarbonyl, 1-methoxycarbonyl-1-methylethoxycarbonyl, ethoxycarbonylmethoxycarbonyl, 1-ethoxycarbonylethoxycarbonyl, 1-ethoxycarbonyl-1-methylethoxycarbonyl, isopropoxycarbonylmethoxycarbonyl, 1-isopropoxycarbonylethoxycarbonyl, and 1-isopropoxycarbonyl-1-methylethoxycarbonyl; (C1-C10 haloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl may include 2-chloroethoxycarbonylmethoxycarbonyl, 1-(2-chloroethoxycarbonyl)ethoxycarbonyl, and 1-(2-chloroethoxycarbonyl)-1-methylethoxycarbonyl; (C3-C10 cycloalkoxy)carbonyl(C1-C5 alkoxy)carbonyl may include cyclopentyloxycarbonylmethoxycarbonyl, 1-cyclopentyloxycarbonylethoxycarbonyl, 1-cyclopentyloxycarbonyl-1-methylethoxycarbonyl, cyclohexyloxycarbonylmethoxycarbonyl, 1-cyclohexyloxycarbonylethoxycarbonyl, and 1-cyclohexyloxycarbonyl-1-methylethoxycarbonyl; (C3-C10 alkenoxy)carbonyl(C1-C5 alkoxy)carbonyl may include allyloxycarbonylmethoxycarbonyl, 1-allyloxycarbonylethoxycarbonyl, and 1-allyloxycarbonyl-1-methylethoxycarbonyl; and (C3-C10 alkynoxy)carbonyl(C1-C5 alkoxy)carbonyl may include propargyloxycarbonylmethoxycarbonyl, 1-propargyloxycarbonylethoxycarbonyl, and 1-propargyloxycarbonyl-1-methylethoxycarbonyl
For the elements or groups represented by R23, R24, R73, or R74, halogen may include fluorine, chlorine, bromine, and iodine; C1-C3 alkyl may include methyl, and ethyl; and C1-C3 haloalkyl may include trifluoromethyl.
For the elements or groups represented by R43, R44, R163, or R164, halogen may include fluorine, chlorine, bromine, and iodine; C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; and C1-C5 haloalkyl may include trifluoromethyl.
For the groups represented by R45, R46, R165, or R166, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered saturated ring, which is formed by combining R45, and R46 or R165 and R166 at their ends, together with the adjacent nitrogen atom, may include aziridine ring, azetidine ring, pyrrolidine ring, and piperidine ring.
For the elements and groups represented by R47, R48, R167, or R168, halogen may include fluorine, chlorine, bromine, and iodine; C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; and C1-C5 haloalkyl may include trifluoromethyl.
For the groups represented by R49, R50, R169, or R170, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl, and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R49 and R50 or R169 and R170 at their ends, together with the adjacent nitrogen atom, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R51, R52, R171, or R172, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R51 and R52 or R171 and R172 at their ends, together with the adjacent nitrogen atom, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R53, R54, R173, or R174, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R53 and R54 or R173 and R174 at their ends, together with the adjacent nitrogen atom, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R55, R57, R175, or R177, C1-C3 alkyl may include methyl, ethyl, and propyl.
For the groups represented by R55, R57, R175, or R177, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; (C1-C5 alkoxy)carbonyl may include methoxycarbonyl, ethoxycarbonyl, and propyloxycarbonyl; (C1-C5 haloalkoxy)carbonyl may include trifluoromethoxycarbonyl and 2,2,2-trifluoroethoxycarbonyl; (C3-C5 cycloalkoxy)carbonyl may include cyclopropyloxycarbonyl; (C3-C5 alkenoxy)carbonyl may include allyloxycarbonyl; and (C3-C5 alkynoxy)carbonyl may include propargyloxycarbonyl.
For the groups represented by R79 or R179, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; C3-C6 alkynyl may include propargyl and 1-methylpropynyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy) carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl.
For the groups represented by R80 or R180, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R79 and R80 or R179 and R180 at their ends, together with the adjacent nitrogen atom, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R81 or R181, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; C3-C6 alkynyl may include propargyl and 1-methylpropynyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl.
For the groups represented by R82 or R182, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; C3-C6 alkynyl may include propargyl and 1-methylpropynyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl.
For the groups represented by R83 or R183, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include; allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R82 and R83 or R182 and R183 at their ends, together with the adjacent nitrogen, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R84 or R184, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; C3-C6 alkynyl may include propargyl and 1-methylpropynyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl.
For the groups represented by R85 or R185, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R84 and R85 or R184 and R185 at their ends, together with the adjacent nitrogen atom, and which contains zero to one oxygen atom or NH group in the ring, may include aziridine ring, azetidine ring, pyrrolidine ring, piperidine ring, morpholine ring, and piperazine ring.
For the groups represented by R86 or R186, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; C3-C6 alkynyl may include propargyl and 1-methylpropynyl; carboxy C1-C5 alkyl may include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl; (C1-C10 alkoxy)carbonyl C1-C5 alkyl may include methoxycarbonylmethyl. ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-butoxycarbonylethyl; (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl may include 2-chloroethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 3-bromopropoxycarbonylmethyl, 1-(2-chloroethoxy)carbonylethyl, and 1-(2,2,2-trifluoroethoxy)carbonylethyl; (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl may include cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl; and (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl may include 4-fluorocyclohexyloxycarbonylmethyl.
For the groups represented by R87 or R187, C1-C5 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl; C1-C5 haloalkyl may include 2-chloroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, and 3-bromopropyl; C3-C8 cycloalkyl may include cyclopentyl, cyclohexyl, and cycloheptyl; C3-C6 alkenyl may include allyl and 1-methylpropenyl; and C3-C6 alkynyl may include propargyl and 1-methylpropynyl.
The 3- to 7-membered ring, which is formed by combining R86 and R87 or R186 and R187 at their ends, together with the adjacent nitrogen atom, may include aziridine ring, azetidine ring, pyrrolidine ring, and piperidine ring.
For the groups represented by E1 or E2, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, and chlorodifluoromethyl; and C3-C6 cycloalkyl optionally substituted with halogen may include cyclopropyl cyclobutyl, and cyclopentyl.
The 4- to 7-membered unsaturated rig, which is formed by combining E1 and E2 at their ends and which contains, together with the atoms attached thereto on Q1, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include those in which tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E1 and E2 
For the groups represented by E3 or E4, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and 3-fluoropropyl; and C3-C6 cycloalkyl optionally substituted with halogen may include cyclopropyl, cyclobutyl, and cyclopentyl.
The 4- or 7-membered saturated or unsaturated ring, which is formed by combining E3 and E4 at their ends and which contains, together with the atoms attached thereto on Q2, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include those in which tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E3 and E4.
For the groups represented by E5, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 3-fluoropropyl, and 4-fluorobutyl.
For the groups or elements represented by E6 or E7, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and 3-fluoropropyl; and C3-C6 cycloalkyl optionally substituted with halogen may include cyclopropyl, cyclobutyl, and cyclopentyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E6 and E7 at their ends and which contains, together with the atoms attached thereto on Q4, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include those in which tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E6 and E7.
For the groups represented by E8 or E9, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and 3-fluoropropyl; and C3-C6 cycloalkyl optionally substituted with halogen may include cyclopropyl, cyclobutyl, and cyclopentyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E8 and E9 at their ends and which contains, together with the atoms attached thereto on Q5, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include those in which tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E8 and E9.
For the groups represented by E10, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and 3-fluoropropyl; and C1-C3 alkoxy optionally substituted with halogen may include methoxy, ethoxy, propoxy, isopropoxy, trifluoromethoxy, and difluoromethoxy.
For the groups represented by E11, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, pentafluoroethyl, and 3-fluoropropyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E10 and E11 at their ends and which contains, together with the atoms attached thereto on Q6, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include those in which tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E10 and E11.
For the elements or groups represented by E44, halogen may include fluorine, chlorine, bromine, or iodine; and C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl
For the groups represented by E12, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the groups represented by E13, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the elements represented by E14, halogen may include chlorine, bromine, and iodine.
For the groups represented by E15, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, and amyl.
For the groups represented by E16, C1-C6 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E15 and E16 at their ends and which contains, together with the atoms attached thereto on Q9, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include those in which tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E15 and E16.
For the groups represented by E17, E18, or E19, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl.
For the groups represented by E20 or E21, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl.
For the groups represented by E22 or E23, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and amyl.
For the groups represented by E24, C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl.
For the groups or elements represented by E25, C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl; and halogen may include fluorine, chlorine, bromine, and iodine.
For the groups represented by E26, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the groups represented by E27, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, isoamyl, pentyl, and hexyl; C3-C6 alkenyl may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C3-C6 alkynyl may include propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, and 1,1-dimethyl-2-propynyl; and optionally substituted benzyl may include benzyl.
For the groups represented by E28, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl
For the groups represented by E29, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, isoamyl, pentyl, and hexyl; C3-C6 alkenyl may include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl; C3-C6 alkynyl may include propargyl, 1-methyl-3-propynyl, 2-butynyl, 3-butynl, and 1,1-dimethyl-2-propynyl; and optionally substituted benzyl may include benzyl.
For the groups represented by E30 or E31, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
The 4- to 7-membered unsaturated ring, which is formed by combining E30 and E31 at their ends and which contains zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include the cases where tetramethylene or trimethylene is formed by E30 and E31.
For the groups represented by E42, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the groups represented by E32, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the elements or groups represented by E33, halogen may include chlorine, bromine, and iodine; C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl and pentafluoroethyl; C1-C3 alkoxy optionally substituted with halogen may include methoxy and ethoxy; and C1-C3 alkylthio optionally substituted with halogen may include methylthio and ethylthio.
For the groups represented by E43, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the groups represented by E34, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the groups represented by E35, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
For the groups represented by E36 or E37, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, isoamyl, pentyl, and hexyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E36 and E37 at their ends and which contains, together with the atoms attached thereto on Q21, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include the cases where tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E36 and E37.
For the groups represented by E38, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, isoamyl, pentyl, and hexyl.
For the groups represented by E39, C1-C3 alkyl optionally substituted with halogen may include methyl, ethyl, propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E38 and E39 at their ends and which contains, together with the atoms attached thereto on Q22, zero to two O, S, SO, SO2 or NH groups (which ring may optionally be substituted with methyl or halogen), may include the cases where tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E38 and E39.
For the groups represented by E40, C1-C6 alkyl may include methyl, ethyl, propyl, isopropyl, isobutyl, butyl, isoamyl, pentyl, and hexyl.
For the groups represented by E41, C1-C3 alkyl may include methyl, ethyl, propyl, and isopropyl; and C3-C6 cycloalkyl may include cyclopropyl, cyclopentyl, and cyclohexyl.
The 4- to 7-membered saturated or unsaturated ring, which is formed by combining E40 and E41 at their ends and which contains, together with the atoms attached thereto on Q23 (which ring may optionally be substituted with methyl or halogen), may include the cases where tetramethylene, trimethylene, or 2,2-dimethyltrimethylene is formed by E40 and E41.
For the present compounds, there may exist geometrical isomers based on the presence of a double bond, or optical isomers and diastereomers based on the presence of at least one asymmetric carbon atom, and all of these isomers and their mixtures are also included within the scope of the present invention.
The preferred substituents from the viewpoint of herbicidal activity may include CH, CCH3, CCl, CBr and N, more preferably CH and N, for A, and Q1, Q2, Q4, Q6, Q14, Q16, Q18, Q19 and Q20 for Q.
When Q is Q1, compounds in which E1 and E2 are combined at their ends to form, together with the atoms attached thereto, a 5- to 7-membered unsaturated ring are preferred, and in particular; compounds in which the unsaturated ring is a 6-membered ring are more preferred.
When Q is Q2, compounds in which E3 and E4 are combined at their ends to form, together with the atoms attached thereto, a 5- to 7-membered saturated or unsaturated ring are preferred, and in particular, compounds in which the saturated or unsaturated ring is a 6-membered ring and D1 and D2 are oxygen are more preferred.
When Q is Q4, compounds in which E6 is C1-C6 alkyl optionally substituted with halogen and E7 is C-C6 alkyl optionally substituted with halogen are preferred, and in particular, compounds in which E6 is methyl substituted with fluorine (e.g., trifluoromethyl, chlorodifluoromethyl, difluoromethyl) or ethyl substituted with fluorine (e.g., pentafluoroethyl, 1,1-difluoroethyl) and E7 is methyl or ethyl are more preferred. In addition, compounds in which E6 and E7 are combined at their ends to form, together with the atoms attached thereto, a 5- or 7-membered saturated or unsaturated ring are preferred, and in particular, compounds in which the saturated or unsaturated ring is a 6-membered ring are more preferred.
When Q is Q6, compounds in which E10 is C1-C6 alkyl optionally substituted with halogen, E11 is C1-C6 alkyl optionally substituted with halogen, and E44 is chlorine or bromine are preferred, and in particular, compounds in which E10 is methyl substituted with fluorine (e.g., trifluoromethyl, chlorodifluoromethyl, difluoromethyl) or ethyl substituted with fluorine (e.g., pentafluoroethyl, 1,1-difluoroethyl) and E11 is methyl or ethyl are more preferred. In addition, compounds in which E10 and E11 are combined at their ends to form, together with the atoms attached thereto, a 5- to 7-membered saturated or unsaturated ring are preferred, and in particular, compounds in which the saturated or unsaturated ring is a 6-membered ring are more preferred.
When Q is Q14, compounds in which D7 is oxygen, E25 is hydrogen, E26 is C1-C3 alkyl optionally with halogen, and E27 is C1-C3 alkyl are preferred, and in particular, compounds in which E26 is methyl substituted with fluorine (e.g., trifluoromethyl, chlorodifluoromethyl, difluoromethyl) or ethyl substituted with fluorine (e.g., pentafluoroethyl, 1,1-difluoroethyl) and E27 is methyl or ethyl are more preferred.
When Q is Q16, compounds in which E30 is C1-C3 alkyl optionally substituted with halogen, E31 is hydrogen or C1-C3 alkyl, and E42 is hydrogen or C1-C3 alkyl are preferred, and in particular, compounds in which E30 is methyl, methyl substituted with fluorine (e.g., trifluoromethyl, chlorodifluoromethyl, difluoromethyl), or ethyl substituted with fluorine (e.g., pentafluoroethyl, 1,1-difluoroethyl), E31 is hydrogen or methyl, and E42 is hydrogen or methyl are more preferred. In addition, compounds in which E30 and E31 are combined at their ends to form, together with the atoms attached thereto, a 5- or 7-membered saturated or unsaturated ring are preferred, and in particular, compounds in which the saturated or unsaturated ring is a 5- or 6-membered ring are more preferred.
When Q is Q18, compounds in which E34 is C1-C3 alkyl optionally substituted with halogen are preferred, and in particular, compounds in which E34 is methyl substituted with fluorine (e.g., trifluoromethyl, chlorodifluoromethyl, difluoromethyl) or ethyl substituted with fluorine (e.g., pentafluoroethyl, 1,1-difluoroethyl) are more preferred.
When Q is Q19, compounds in which V1 is xe2x80x94CH2xe2x80x94 or xe2x80x94CH2xe2x80x94CH2xe2x80x94 are preferred.
When Q is Q20, compounds in which E35 is C1-C3 alkyl optionally substituted with halogen, Z2 is nitrogen, and V2 is xe2x80x94CH2xe2x80x94CH2xe2x80x94 or xe2x80x94CHxe2x95x90CHxe2x80x94 are preferred, and in particular, compounds in which E35 is methyl substituted with fluorine (e.g., trifluoromethyl, chlorodifluoromethyl, difluoromethyl) or ethyl substituted with fluorine (e.g., pentafluoroethyl, 1,1-difluoroethyl) are more preferred.
Specific examples of the preferred compounds are recited below:
Methyl 3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
Ethyl 3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
Isopropyl 3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetraydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
Methyl 3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2 3,6-tetrahydropyrimidin-1-yl]-6-nitrobenzo[b]furan-5-carboxylate;
Ethyl 3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-6-nitrobenzo[b]furan-5-carboxylate;
Methyl 6-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
Ethyl 6-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
Methyl 7-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
Ethyl 7-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-carboxylate;
3-(5-Methoxybenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-(5-Methoxy-6-nitrobenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-(6-Chloro-5-methoxybenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-(7-Chloro-5-methoxybenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[5-(Allyloxy)benzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[5-(Allyloxy)-6-nitrobenzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[5-(Allyloxy)-6-chlorobenzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[5-(Allyloxy)-7-chlorobenzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
1-Methyl-3-[5-(prop-2-ynyloxy)benzo[b]furan-3-yl]-6-(trifluoroethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
1-Methyl-3-[6-nitro-5-(prop-2-ynyloxy)benzo[b]furan-3-yl]-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[6-Chloro-5-(prop-2-ynyloxy)benzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[7-Chloro-5-(prop-2-ynyloxy)benzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
Ethyl 2-({3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-yl}oxy)propanoate;
Ethyl 2-({6-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-yl}oxy)propanoate;
Ethyl 2-({7-chloro-3-[3-methyl-2,6-dioxo-4-(trifuoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-yl}oxy)propanoate;
1-Methyl-3-[5-(methylthio)benzo[b]furan-3-yl]-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
1-Methyl-3-[5-(methylthio)-6-nitrobenzo[b]furan-3-yl]-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[6-Chloro-5-(methylthio)benzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-[7-Chloro-5-(methylthio)benzo[b]furan-3-yl]-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
Ethyl 2-({3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-6-nitrobenzo[b]furan-5-yl}thio)propanoate;
Ethyl 2-({6-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidim-1-yl]benzo[b]furan-5-yl}thio)propanoate;
Ethyl 2-({7-chloro-3-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzo[b]furan-5-yl}thio)propanoate;
3-(5,7-Dichlorobenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;
3-(5-Bromo-7-chlorobenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione; and
3-(7-Chloro-5-methylbenzo[b]furan-3-yl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione.
The present compounds can be produced, for example, by Producing Processes 1 to 27 as described below.
In the process, compound a-1 of the general formula: 
wherein T, A, Y, R1, R2, R3, and R4 are as defined above, is reacted with acid anhydride a-5 of the general formula: 
wherein E1 and E2 are as defined above.
The reaction is carried out without solvent or in a solvent. The reaction temperature is usually in the range of 50xc2x0 C. to 200xc2x0 C. The reaction time is usually in the range of 1 to 100 hours. The amounts of reagents to be used in the reaction are 1 mole of acid anhydride a-5 relative to 1 mole of compound a-1, which is the stoichiometric ratio but can be freely changed depending upon the reaction conditions.
The solvent which can be used may include aliphatic hydrocarbons such as hexane, heptane, octane, and ligroin; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene; ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; organic acids such as acetic acid and propionic acid; acid amides such as N,N-dimethylformamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof. In addition, acids such as p-toluenesulfonic acid can also be used as a reaction catalyst.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography. (see JP-A 55-139359.)
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, D1, D2, E3, E4, T, A, and Y are as defined above, R200 is C1-C5 alkyl (e.g., methyl, ethyl) or hydrogen.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 61-27985, or for example, by the following processes.
1). Process of Producing Compound a-2 from Compound a-1
Compound a-2 can be produced by converting compound a-1 into an isocyanate or isothiocyanate derivative in a solvent or without solvent.
Agent for conversion into isocyanate or isothiocyanate derivatives: phosgene, trichloromethyl chloroformate, oxalyl chloride, thiophosgene, etc.
Amount of agent for conversion into isocyanate or isothiocyanate derivatives: 1 equivalent to an excess amount relative to 1 mole of compound a-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; etc.
Reaction temperature: room temperature to the reflux temperature of the agent for conversion into isocyanate or isothiocyanate derivatives
Reaction time: a moment to 48 hours.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound a-3 from Compound a-2
Compound a-3 can be produced by reacting compound a-2 with compound a-6 of the general formula: 
wherein D1, E3, E4, and R200 are as defined above, in a solvent in the presence of a base.
Amount of compound a-6: 1 to 5 moles relative to 1 mole of compound a-2
Kind of base: inorganic bases such as sodium hydride and potassium carbonate; organic bases such as triethylamine; metal alcoholates such as sodium methylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound a-2
Solvents: ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; alcohols such as ethanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9215xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound a-4 may be directly obtained depending upon the reaction conditions of this process.
3) Process of Producing Compound a-4 from Compound a-3
Compound a-4 can be produced by reacting compound a-3 in a solvent in the presence of a base.
Kind of base: inorganic bases such as sodium hydride; metal alcoholates such as sodium methylate; etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound a-3
Solvent: ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; alcohols such as methanol and ethanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, R200, D1, D2, E3, E4, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 61-27985, or for example, by the following processes.
1) Process of Producing Compound b-3 from Compound a-2
Compound b-3 can be produced by reacting compound a-2 with compound b-5 of the general formula: 
wherein D1, E3, E4, and R200 are as defined above, in a solvent in the presence of a base.
Amount of compound b-5: 1 to 5 moles relative to 1 mole of compound a-2
Kind of base: inorganic bases such as sodium hydride and potassium carbonate; organic bases such as triethylamine; metal alcoholates such as sodium methylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound a-2
Solvent: ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; alcohols such as ethanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9215xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound b-4 may be directly obtained depending upon the reaction conditions of this process.
2) Process of Producing Compound b-4 from Compound b-3
Compound b-4 can be produced by reacting compound b-3 in a solvent in the presence of a base.
Kind of base: inorganic bases such as sodium hydride; metal alcoholates such as sodium methylate; etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound b-3
Solvent: ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; alcohols such as methanol and ethanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, D3, E5, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in WO87/03873, or for example, by the following processes.
1) Process of Producing Compound c-1 from Compound a-1
Compound c-1 can be produced from compound a-1 according to the process as described above in Producing Process 2, Step 1).
2) Process of Producing Compound c-2 from Compound c-1
Compound c-2 can be produced by reacting compound c-1 and trimethylsilyl azide in a solvent or without solvent.
Amount of trimethylsilyl azide: 1 to 3 moles relative to 1 mole of compound c-1
Solvent: benzene, toluene, chlorobenzene, etc.
Reaction temperature: room temperature to the reflux temperature
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound c-3 from Compound c-2
Compound c-3 can be produced by reacting compound c-2 and compound c-4 of the general formula:
M1xe2x80x94E5xe2x80x83xe2x80x83c-4
wherein E5 is as defined above and M1 is chlorine, bromine, iodine, or methanesulfonyloxy, in a solvent in the presence of a base.
Amount of compound c-4: 1 to 3 moles relative to 1 mole of compound c-2
Kind of base: sodium hydride, potassium carbonate, etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound c-2
Solvent: N,N-dimethylformamide, tetrahydrofuran, etc.
Reaction temperature: room temperature to 150xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R201 is methoxy, ethoxy or dimethylamino; and R1, R2, R3, R4, E6, E7, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 60-149571, or for example, by the following processes.
1) Process of Producing Compound d-1 from Compound a-1
Compound d-1 can be produced by converting compound a-1 into a diazonium salt with sodium nitrite in the presence of an acid and then reacting the diazonium salt with a reducing agent such as tin (II) chloride. (see Organic Synthesis Collective Volume 1, p. 442.)
(Diazonium Salt Formation)
Amount of sodium nitrite: 1 to 2 moles relative to 1 mole of compound a-1
Kind of acid: hydrochloric acid etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound a-1
Solvent: water, ethanol, hydrochloric acid, etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 24 hours
(Reduction Reaction)
Kind of reducing agent: tin (II) chloride etc.
Amount of reducing agent: 3 to 10 moles relative to 1 mole of compound a-1
Solvent: hydrochloric acid etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound d-3 from Compound d-1
Compound d-3 can be produced by reacting compound d-1 and compound d-5 of the general formula: 
wherein E7 and R201 are as defined above and R202 is methyl or ethyl, in a solvent, if necessary, in the presence of a base, to give intermediate d-2 and then reacting the intermediate d-2 in the presence of a base.
Intermediate d-2 may be isolated.
(Reaction of Compound d-1 into Compound d-2)
Amount of compound d-5: 1 to 3 moles relative to 1 mole of compound d-1.
Kind of base: organic bases such as triethylamine and pyridine; metal alcoholates such as sodium methylate and sodium ethylate; inorganic bases such as sodium hydroxide and potassium carbonate; etc.
Solvent: aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene; alcohols such as ethanol and isopropanol; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran and 1,4-dioxane; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
(Reaction of Compound d-2 into Compound d-3)
Kind of base: organic bases such as triethylamine and pyridine; metal alcoholates such as sodium methylate and sodium ethylate; inorganic bases such as sodium hydroxide and potassium carbonate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound a-1
Solvent: aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene; alcohols such as ethanol and isopropanol; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran and 1,4-dioxane; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound d-4 from Compound d-3
Compound d-4 can be produced by reacting compound d-3 with compound d-6 of the general formula:
M1xe2x80x94E6xe2x80x83xe2x80x83d-6
wherein E6 and M1 are as defined above, in a solvent in the presence of a base.
Amount of compound d-6: 1 to 3 moles relative to 1 mole of compound d-3
Kind of base: sodium hydride, potassium carbonate, etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound d-3
Solvent: N,N-dimethylformamide, tetrahydrofuran, etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound d-3 can also be produced according to the following scheme. (see JP-A 7-503253.) 
wherein R1, R2, R3, R4, E7, T, A, and Y are as defined above.
1) Process of Producing Compound e-1 from Compound d-1
Compound e-1 can be produced by reacting compound d-1 with compound e-3 of the general formula: 
wherein E7 is as defined above, in a solvent.
Amount of compound e-3: 1 to 10 moles relative to 1 mole of compound d-3
Solvent: water; alcohols such as ethanol and t-butanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9215xc2x0 C. to 70xc2x0 C.
Reaction time: a moment to 24 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound e-1 can also be used as such for the reaction in the next step without isolation.
2) Process of Producing Compound e-2 from Compound e-1
Compound e-2 can be produced by reacting compound e-1 with an alkali metal cyanate, in a solvent, if necessary, in the presence of an acid.
Kind of alkali metal cyanate: NaOCN, KOCN, etc.
Amount of alkali metal cyanate: 1 to 3 moles relative to 1 mole of compound e-1
Kind of acid: organic acids such as acetic acid
Amount of acid: 0.01 to 1 mole relative to 1 mole of compound e-1
Solvent: water; alcohols such as ethanol and t-butanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9215xc2x0 C. to 80xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallzation or column chromatography.
Compound e-2 can also be used as such in the next step without isolation.
3) Process of Producing Compound d-3 from Compound e-2
Compound d-3 can be produced by oxidizing compound e-2 with an oxidizing agent such as halogen, hypohalous acid, or hypohalite in a solvent.
Kind of oxidizing agent: chlorine, hypochlorous acid, sodium hypochlorite, etc.
Amount of oxidizing agent: 1 to 3 moles relative to 1 mole of compound e-2
Solvent: water; alcohols such as ethanol and t-butanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9215xc2x0 C. to 60xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example; the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R1, R3, R4, E10, E11, T, A, and Y are as defined above; E144 is halogen; and R203 is methyl or ethyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 60-233061, or for example, by the following processes.
1) Process of Producing Compound f-2 from Compound d-1
Compound f-2 can be produced by reacting compound d-1 with compound f-4 of the general formula: 
wherein E10, E11, and R203 are as defined above, in a solvent, if necessary, in the presence of an acid.
Amount of compound f-4: 1 to 10 moles relative to 1 mole of compound d-1
Solvent: water; alcohols such as ethanol, isopropanol and butanol; aromatic hydrocarbons such as benzene and toluene; organic acids such as acetic acid and propionic acid; and mixtures thereof; etc.
Kind of acid: p-toluenesulfonic acid, hydrochloric acid, acetic acid, etc.
Amount of acid: 0.0001 mole to an excess amount relative to 1 mole of compound d-1
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound f-3 from Compound f-2
Compound f-3 can be produced by reacting compound f-2 with a halogenating agent in a solvent or without solvent under normal pressure or increased pressure.
Kind of halogenating agent: phosphorous oxychloride, phosphorous pentachloride, oxalyl chloride, phosgene, trichloromethyl chloroformate, etc.
Amount of halogenating agent: 1 mole to an excess amount relative to 1 mole of compound f-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; etc.
Reaction temperature: 50xc2x0 C. to 250xc2x0 C.
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
The compounds wherein E10 is CF2H can also be produced according to the following scheme: 
wherein R1, R2, R3, R4, E11, E144, T, A, and Y are defined above.
1) Process of Producing Compound g-2 from Compound g-1
Compound g-2 can be produced by reacting compound g-1 with a Vilsmeier reagent (prepared from dimethylformamide and a halide such as phosphorus oxychloride, phosphorus pentachloride, oxalyl chloride, phosgene or trichloromethyl chloroformate; see Jikken Kagaku Koza, 4th Edition, 21, p. 110) in a solvent or without solvent.
Amount of Vilsmeier reagent: 1 to 20 moles relative to 1 mole of compound g-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 150xc2x0 C.
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaing the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound g-3 from Compound g-2
Compound g-3 can be produced by reacting compound g-2 with a fluorinating agent in a solvent.
Kind of fluorinating agent: dimethylaminosulfur trifluoride etc.
Amount of fluorinating agent: 1 to 10 moles relative to 1 mole of compound g-2
Solvent: halogenated aromatic hydrocarbons such as chlorobenzene; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to room temperature
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E12, D4, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 60-109578, or for example, by the following processes.
1) Process of Producing Compound h-1 from Compound d-1
Compound h-1 can be produced by reacting compound d-1 with an acylating agent selected from compound h-3 of the general formula: 
wherein E12 is as defined above and R204 is hydrogen, methyl, or ethyl, compound h-4 of the general formula: 
wherein E12 is as defined above, and compound h-5 of the general formula: 
wherein E12 is as defined above, in a solvent or without solvent.
Amount of acylating agent: 1 to 5 moles relative to 1 mole of compound d-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound h-2 from Compound h-1
Compound h-2 can be produced by reacting compound h-1 with compound h-6 of the general formula: 
wherein D4 is as defined above, in a solvent in the presence of a base.
Amount of compound h-6: 1 to 5 moles of compound h-1
Kind of base: organic bases such as ti4triethylamine and pyridine; inorganic bases such as potassium carbonate; etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound h-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to room temperature
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E13, T, A, and Y are as defined above; E114 is halogen; and R205 is methyl or ethyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 6-145011, or for example, by the following processes.
1) Process of Producing Compound i-1 from Compound a-1
Compound i-1 can be produced by reacting compound a-1 with a chloroformate i-5 of the general formula:
ClCOOR205xe2x80x83xe2x80x83i-5
wherein R205 is as defined above, in a solvent in the presence of a base.
Amount of chloroformate i-5: 1 to 10 moles relative to 1 mole of compound a-1
Kind of base: N,N-dimethylaniline, N,N-diethylaniline, etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound a-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound i-2 from Compound i-1
Compound i-2 can be produced by reacting compound i-1 with compound i-6 of the general formula: 
wherein E13 is as defined above and M6 is chlorine or bromine, in a solvent in the presence of lithium bis(trimethylsilyl)amide.
Amount of compound i-6: 1 to 10 moles relative to 1 mole of compound i-1
Amount of lithium bis(trimethylsilyl)amide: 1 to 10 moles relative to 1 mole of compound i-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound i-3 from Compound i-2
Compound i-3 can be produced by reacting compound i-2 with a halogenating agent in a solvent.
Kind of halogenating agent: chlorine, bromine, etc.
Amount of halogenating agent: 1 mole to large excess relative to 1 mole of compound i-2
Solvent: halogenated aromatic hydrocarbons such as chlorobenzene; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound i-4 from Compound i-3
Compound i-4 can be produced by reacting compound i-3 with a base in a solvent.
Kind of base: organic bases such as triethyl amine and 1,8-diazabicylo[5.4.0]undec-7-ene; etc.
Amount of base: 1 mole to large excess relative to 1 mole of compound i-3
Solvent: dimethylsulfoxide etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E15, E16, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 60-104073, or for example, by the following processes.
1) Process of Producing Compound j-1 from Compound d-1
Compound j-1 can be produced by reacting compound d-1 with compound j-3 of the general formula: 
wherein E15 and E16 are as defined above, in a solvent, if necessary, in the presence of an acid.
Amount of compound j-3: 1 to 5 moles relative to 1 mole of compound d-1
Solvent: toluene, ethanol, acetic acid, tetrahydrofuran, etc.
Acid: p-toluenesulfonic acid etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound j-2 from Compound j-1
Compound j-2 can be produced by reacting compound j-1 with an oxidizing agent in a solvent in the presence of a pyridine.
Amount of pyridine: 1 to 2 moles relative to 1 mole of compound j-1
Kind of oxidizing agent: copper (II) sulfate etc.
Amount of oxidizing agent: 1 to 5 moles relative to 1 mole of compound j-1
Solvent: toluene, ethanol, acetic acid, tetrahydrofuran, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E17, E18, E19, D5, T, A, and Y are as defined above and R206 is methyl or ethyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 63-183567, or for example, by the following processes.
1) Process of Producing Compound k-1 from Compound a-1
Compound k-1 can be produced from compound a-1 according to the process as described above in Producing Process 2, Step 1).
2) Process of Producing Compound k-2 from Compound k-1
Compound k-2 can be produced by reacting compound k-1 with compound k-5 of the general formula: 
wherein E18, E19, and R206 are as defined above, in a solvent in the presence of a base.
Amount of compound k-5: 1 to 2 moles relative to 1 mole of compound k-1
Kind of base: triethylamine, potassium carbonate, sodium hydride, sodium methylate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound k-1
Solvent: toluene, ethanol, tetrahydrofuran, N,N-dimethylformamide, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound k-3 may be obtained directly depending upon the reaction conditions of this process.
3) Process of Producing Compound k-3 from Compound k-2
Compound k-3 can be produced by reacting compound k-2 in a solvent in the presence of a base.
Kind of base: potassium carbonate, sodium hydride, sodium methylate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound k-2
Solvent: toluene, ethanol, tetrahydrofuran, N,N-dimethylformamide, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound k-4 from Compound k-3
Compound k-4 can be produced by reacting compound k-3 with compound k-6 of the general formula:
M7xe2x80x94E17xe2x80x83xe2x80x83k-6
wherein E7 is as defined above and M7 is iodine, bromine, or chlorine, in a solvent in the presence of a base.
Amount of compound k-6: 1 to 2 molesrelative to 1 mole of compound k-3
Kind of base: triethylamine, potassium carbonate, sodium hydride, sodium methylate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound k-3
Solvent: toluene, ethanol, tetrahydrofuran, N,N-diinethylformamide, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to ost-treatments, for example, the reaction mixture is poured into water, and he deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaiing the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E20, E21, D6, T, A, and Y are as defined above and R207 is methyl or ethyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in WO87/62357, or for example, by the following processes.
1) Process of Producing Compound l-1 from Compound a-1
Compound l-1 can be produced from compound a-1 according to the process as described above in Producing Process 2, Step 1).
2) Process of Producing Compound l-2 from Compound l-1
Compound l-2 can be produced by reacting compound l-1 with compound l-4 of the general formula. 
wherein E20, E21, and R207 are as defined above, in a solvent in the presence of a base.
Amount of compound l-4: 1 to 2 moles relative to 1 mole of compound l-1
Kind of base: triethylamine, potassium carbonate, sodium hydride, sodium methylate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound l-1
Solvent: toluene, ethanol, tetrahydrofuran, N,N-dimethylformamide, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound l-3 may be obtained directly depending upon the reaction conditions of this process.
3) Process of Producing Compound l-3 from Compound l-2
Compound l-3 can be produced by reacting compound l-2 in a solvent in the presence of a base.
Kind of base: potassium carbonate, sodium hydride, sodium methylate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound l-2
Solvent: toluene, ethanol, tetrahydrofuran, N,N-dimethylformamide, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E22, E23, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 61-103801, or for example, by the following processes.
1) Process of Producing Compound m-1 from Compound a-1
Compound m-1 can be produced by reacting compound a-1 with acid anhydride m-2 of the general formula: 
wherein E22 and E23 are as defined above, usually without solvent, or in a solvent, if necessary, in the presence of an acid.
The reaction temperature is usually in the range of 50xc2x0 C. to 200xc2x0 C. The reaction time is usually in the range of 1 to 100 hours. The amounts of agents to be used in the reaction are 1 mole of acid anhydride m-2 relative to 1 mole of compound a-1, which; is the stoichiometric ratio but can be freely changed depending upon the reaction conditions.
The solvent which can be used may include aliphatic hydrocarbons such as hexane, heptane, octane, and ligroin; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, and mesitylene; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene; ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl t-butyl ether; nitro compounds such as nitromethane and nitrobenzene; organic acids such as acetic acid and propionic acid; acid amides such as N,N-dimethylformamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof As the acid, p-toluenesulfonic acid can be used.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E24, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in WO86/00072, or for example, by the following processes.
1) Process of Producing Compound n-1 from Compound a-1
Compound n-1 can be produced by converting compound a-1 into a diazonium salt with sodium nitrite in a solvent in the presence of an acid and then reacting the diazonium salt with compound n-5 of the formula: 
in a solvent in the presence of a base.
(Diazonium salt formation)
Amount of sodium nitrite: 1 to 2 moles relative to 1 mole of compound a-1
Kind of acid: hydrochloric acid etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound a-1
Solvent: water, ethanol, hydrochloric acid, etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 24 hours
(Reaction with compound n-5)
Amount of compound n-5: 1 to 5 moles relative to 1 mole of compound a-1
Kind of base: sodium acetate etc.
Amount of base: 0.8 to 3 moles relative to 1 mole of acid used in the forgoing step
Solvent: ethanol, water, etc.
Reaction temperature: 0xc2x0C. to 60xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound n-2 from Compound n-1
Compound n-2 can be produced by reacting compound n-1 in a solvent in the presence of a base.
Kind of base: sodium hydroxide, potassium hydroxide, etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound n-1
Solvent: ethanol, N,N-dimethylformamide, water, and mixtures thereof; etc.
Reaction temperature: 0xc2x0 C. to 110xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound n-3 from Compound n-2
Compound n-3 can be produced by reacting compound n-2 in a solvent in the presence of thioacetic acid.
Amount of thioacetic acid: 0.1 to 10 moles relative to 1 mole of compound n-2
Solvent: xylene etc.
Reaction temperature: reflux temperature
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound n-4 from Compound n-3
Compound n-4 can be produced by reacting compound n-3 with compound n-6 of the general formula:
M8xe2x80x94E24xe2x80x83xe2x80x83n-6
wherein E24 is as defined above and M8 is iodine, bromine, or chlorine, in a solvent in the presence of a base.
Amount of compound n-6: 1 to 10 moles relative to 1 mole of compound n-3
Kind of base: potassium carbonate, sodium hydride, etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound n-3
Solvent: acetone, tetrahydrofuran, N,N-dimethylformamide, etc.
Reaction temperature: 0xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E25, E26, E27, T, A, and Y are as defined above, and R208 and R209 are independently C1-C5 alkyl (e.g., methyl, ethyl, propyl).
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 5-4959 and JP-A 63-41466, or for example, by the following processes.
1) Process of Producing Compound o-1 from Compound a-1
Compound o-1 can be produced from compound a-1 and chloroformate o-4 of the general formula:
ClCOOR208xe2x80x83xe2x80x83o-4
wherein R208 is as defined above, according to the process as described above in Producing Process 8, Step 1).
2) Process of Producing Compound o-11from Compound o-1
Compound o-11 can be produced by reacting compound o-1 with compound o-5 of the general formula: 
wherein E25, E26, and R209are as defined above, in a solvent in the presence of a base.
Amount of compound o-5: 0.9 to 10 moles relative to 1 mole of compound o-1
Kind of base: inorganic bases such as sodium hydride; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound o-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; and mixtures thereof; etc.
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound o-11can also be used as such for the reaction in the next step without isolation.
3) Process of Producing Compound o-2 from Compound o-11
Compound o-2 can be produced by reacting compound o-11 in a solvent in the presence of a base.
Kind of base: inorganic bases such as sodium hydride and potassium carbonate; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10moles relative to 1 mole of compound o-11
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; sulfur compound such as dimethylsulfoxide; and mixtures thereof
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound o-2 can also be used as such for the reaction in the next step without isolation.
4) Process of Producing Compound o-3 from Compound o-2
Compound o-3 can be produced by reacting compound o-2 with compound o-6 of the general formula:
M9xe2x80x94E27xe2x80x83xe2x80x83o-6
wherein E27 is as defined above and M9 is iodine, bromine, chlorine, methanesulfonyloxy, or 2,4-dinitrophenoxy, in a solvent in the presence of a base.
Amount of compound o-6: 0.9 to 10 moles relative to 1 mole of compound o-2
Kind of base: inorganic bases such as sodium hydride, potassium carbonate, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound o-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, D7, E25, E26, E27, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 63-41466, or for example, by the following processes.
1) Process of Producing Compound p-1 from Compound a-1
Compound p-1 can be produced from compound a-1 according to the process as described above in Producing Process 2, Step 1).
2) Process of Producing Compound p-2 from Compound p-1
Compound p-2 can be produced by reacting compound p-1 with compound p-7 of the general formula: 
wherein E25, E26, and R209 are as defined above, in a solvent in the presence of a base.
Amount of compound p7: 0.9 to 10 moles relative to 1 mole of compound p-1
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound p-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; and mixtures thereof; etc.
Reaction temperature: xe2x88x9240xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound p-2 can also be used as such for the reaction in the next step without isolation.
3) Process of Producing Compound p-3 from Compound p-2
Compound p-3 can be produced by reacting compound p-2 with compound o-6 of the general formula:
M9xe2x80x94E27xe2x80x83xe2x80x83o-6
wherein E27 and M9 are as defined above, in a solvent in the presence of a base.
Amount of compound o-6: 0.9 to 10 moles relative to 1 mole of compound p-2
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound p-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, D7, E25, E26, E27, T, A, and Y as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 63-41466, or for example, by the following processes.
1) Process of Producing Compound p-4 from Compound p-1
Compound p-4 can be produced by reacting compound p-1 with ammonia in a solvent.
Amount of ammonia: 1 mole to large excess relative to 1 mole of compound p-1
Solvent: water, methanol, ethanol, tetrahydrofuran, 1,4-dioxane, etc.
Reaction temperature: xe2x88x9220xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 24 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound p-2 from Compound p-4
Compound p-2 can be produced by reacting compound p-4 with compound p-9 of the general formula: 
wherein E25, E26, and R209 are as defined above and R210 is methyl, in a solvent in the presence of a base.
Amount of compound p-9: 0.9 to 10 moles relative to 1 mole of compound p-4
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound p-4
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound p-2 can also be used as such for the reaction in the next step without isolation.
3) Process of Producing Compound p-3 from Compound p-2
Compound p-3 can be produced by reacting compound p-2 with compound o-6 of the general formula:
M9xe2x80x94E27xe2x80x83xe2x80x83o-6
wherein E27 and M9 are as defined above, in a solvent in the presence of a base.
Amount of compound o-6: 0.9 to 10 moles relative to 1 mole of compound p-2
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound p-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, D7, E28, E29, A, T, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 6-92943, or for example, by the following processes.
1) Process of Producing Compound p-6 from Compound p-5
Compound p-6 can be produced by reducing compound p-5 in a solvent.
Kind of reducing agent: NaBH4 etc.
Amount of reducing agent: 1 to 10 moles relative to 1 mole of compound p-5
Solvent: water, methanol, ethanol, acetic acid, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E30, E31, E42, T, A, and Y are as defined above, and R211 is hydrogen, methyl, or ethyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 9-323977 and WO98/17632, or for example, by the following processes.
1) Process of Producing Compound w-1 from Compound a-1
Compound w-1 can be produced from compound a-1 according to the process as described above in Producing Process 5, Step 1).
2) Process of Producing Compound w-2 from Compound w-1
Compound w-2 can be produced by reacting compound w-8 of the general formula: 
wherein E30 and E42 are as defined above and M10 is iodine, bromine, or chlorine, with water in the presence of a base to form compound w-9 of the general formula: 
wherein E30 and E42 are as defined above (reaction 1), and then reacting the carbonyl derivative with compound w-1 (reaction 2).
(Reaction 1)
Reaction 1 is usually carried out in a solvent. The reaction temperature is usually in the range of 20xc2x0 C. to 100xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of agents to be used in the reaction are 2 moles of each of the water and base relative to 1 mole compound w-8, which is ideal but can be freely changed depending upon the reaction conditions.
As the base to be used, both organic bases and inorganic bases can be used, examples of which are sodium acetate and potassium acetate.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile; amides such as N,N-di-methylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof
(Reaction 2)
Reaction 2 is usually carried out in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 C. to 200xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of agents to be used in the reaction are 1 mole of compound w-1 relative to 1 mole of compound w-8, which is ideal but can be freely changed depending upon the reaction conditions. Depending upon the conditions, salts of compound w-1, such as hydrochloride salt and sulfate salt, can also be used.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile; amides such as N,N-di-methylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound w-3 from Compound w-2 (Route 1)
Compound w-3 can be produced by reacting compound w-2 with phosphorane compound w-10 of the general formula: 
wherein E31 is as defined above; R213 is methyl or ethyl; and Ar is optionally substituted phenyl (e.g., phenyl), in a solvent.
This reaction is usually carried out in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 C. to 150xc2x0 C, preferably 0xc2x0 C. to 100xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of agents to be used in the reaction are 1 mole of compound w-10 relative to 1 mole of compound w-2, which is ideal but can be freely changed depending upon the reaction conditions.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile; amides such as N,N-di-methylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound w-4 from Compound w-2 (Route 2)
Compound w-4 can be produced by reacting compound w-2 with compound w-11 of the general formula: 
wherein E31 and R211 are as defined above, in the presence of a base.
This reaction is usually carried out in a solvent. The reaction temperature is usually in the range of 20xc2x0 C. to 200xc2x0 C., preferably 40xc2x0 C. to 150xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of agents to be used in the reaction are usually 1 to 10 moles of compound w-11, preferably 1 to 2 moles of compound w-11, which is ideal, relative to 1 mole of compound w-2. The amount of base is usually 1 mole to large excess, preferably 1 to 10 moles, relative to 1 mole of compound w-11
The base which can be used may include organic bases such as triethylamine and tributylamine.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile; amides such as N,N-di-methylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining he desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
5) Process of Producing Compound w-3 from Compound w-4
Compound w-3 can be produced by reacting compound w-4, if necessary, in the presence of a base or acid, or in an acid-base mixed system.
This reaction is usually carried out in a solvent. The reaction temperature is usually in the range of 20xc2x0 C. to 200xc2x0 C., preferably 40xc2x0 C. to 150xc2x0 C. The reaction time is usually in the range of a moment to 96 hours.
The kind of base used, if necessary, may include organic bases such as pyridine; and metal alcoholates such as sodium methylate. The amount of base is usually 1 mole to large excess, preferably 1 to 10 moles, which is ideal, relative to 1 mole of compound w-4.
The kind of add used, if necessary, may include organic acids such as acetic acid and benzoic acid; and p-toluenesulfonic acid. The amount of acid is usually 1 mole to large excess, preferably 1 to 10 moles, which is ideal, relative to 1 mole of compound w-4.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile; amides such as N,N-di-methylformamide; alcohols such as methanol, ethanol, and isopropanol; and mixtures thereof.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound w-7 (i.e., compound w-2 wherein E42 is H) can also be produced according to the following scheme: 
wherein R1, R2, R3, R4, E30, T, A, and Y are as defined above, and R214 is methyl or ethyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 9-323977, or for example, by the following processes.
6) Process of Producing Compound w-5 from Compound a-1 (see Tetrahedron, vol. 35, p. 2013 (1979))
Compound w-5 can be produced by converting compound a-1 into a diazonium salt with sodium nitrite in a solvent in the presence of an acid, and then reacting the diazonium salt with compound w-12 of the general formula: 
wherein E30 and R214 are as defined above, in a solvent in the presence of a base.
(Diazonium salt formation)
Amount of sodium nitrite: 1 to 2 moles relative to 1 mole of compound a-1
Kind of acid: hydrochloric acid etc.
Amount of acid: 1 to 100 moles relative to 1 mole of compound a-1
Solvent: water, ethanol, hydrochloric acid, etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 24 hours
(Reaction with compound w-12)
Amount of compound w-12: 1 to 5 moles relative to 1 mole of compound a-1
Kind of base: sodium acetate etc.
Amount of base: 0.8 to 3 moles relative to 1 mole of acid used in the forgoing step
Solvent: ethanol, water, etc.
Reaction temperature: 0xc2x0 C. to 60xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
6) Process of Producing Compound w-6 from Compound w-5
Compound w-6 can be produced by reacting compound w-5 in a solvent in the presence of a base.
The reaction temperature is usually in the range of 0xc2x0 C. to 150xc2x0 C.
The reaction time is usually in the range of a moment to 72 hours. The amounts of agents to be used in the reaction are 1 mole of base relative to 1 mole of compound w-5, which is ideal but can be freely changed, if necessary. The base may include inorganic bases such as sodium hydroxide, lithium hydroxide, lithium hydroxide monohydrate, barium hydroxide, and potassium hydroxide.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; nitrites such as acetonitrile; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
7) Process of Producing Compound w-7 from Compound w-6
Compound w-7 can be produced by heating compound w-6 in a solvent.
The reaction temperature is usually in the range of 50xc2x0 C. to 200xc2x0 C. The reaction time is usually in the range of a moment to 72 hours.
The solvent which can be used may include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; nitrites such as acetonitrile; amides such as N,N-dimethylformamride; alcohols such as methanol, ethanol and isopropanol; nitrogen-containing aromatic compounds such as pyridine and picoline; sulfur compounds such as dimethylsulfoxide; tertiary amines such as N,N-dimethylailine; water; and mixtures thereof.
In this reaction, metals such as copper powder may be used as a catalyst, if necessary.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E32, E33, E43, T, A, and Y are as described above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 6-25186, or for example, by the following processes.
1) Process of Producing Compound r-1 from Compound a-1
Compound r-1 can be produced by converting compound a-1 into an isothiocyanate derivative in a solvent or without solvent.
Agent for conversion into isothiocyanate derivatives: thiophosgene etc.
Amount of agent for conversion into isothiocyanate derivatives: 1 equivalent to an excess amount relative to 1 mole of compound a-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; etc.
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound r-2 from Compound r-1
Compound r-2 can be produced by reacting compound r-1 with compound r-6 of the general formula: 
wherein E32 and E43 are as defined above and R215 is methyl, ethyl, or propyl in a solvent in the presence of a base.
Amount of compound r-6: 0.9 to 10 moles relative to 1 mole of compound r-1
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound r-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chrormatography.
3) Process of Producing Compound r-3 from Compound r-2
Compound r-3 can be produced by reacting compound r-2 with Raney nickel in a solvent in the presence of a base.
Amount of Raney nickel: 1 to 20 moles relative to 1 mole of compound r-2
Kind of base: nitrogen-containing compounds such as pyridine; organic bases such as triethylamine; ammonia; etc.
Amount of base: 0. 1 to 20 moles relative to compound r-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; alcohols such as methanol and ethanol; water; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound r-4 from Compound r-3
Compound r-4 can be produced by reacting compound r-3 in a solvent in the presence of a base.
Kind of base: metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 1 to 20 moles relative to compound r-3
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; alcohols such as methanol and ethanol; water; and mixtures thereof; etc.
Reaction temperature: 20xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
5) Process of Producing Compound r-5 from Compound r-4
Compound r-5 can be produced by reacting compound r-4 with an acylating agent selected from compound r-7 of the general formula: 
wherein E33 is as defined above, or compound r-8 of the general formula: 
wherein E33 is as defined above, in a solvent.
Amount of acylating agent: 1 to 5 moles relative to 1 mole of compound r-4
Solvent: organic acids such as acetic acid and propionic acid; etc.
Reaction temperature: the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, E34, T, A, and Y are as defined above.
The reaction can be carried out, for example, according to the process as described in JP-A 4-356463, or for example, by the following process.
1) Process of Producing Compound s-1 from Compound a-1
Compound s-1 can be produced by reacting compound a-1 with acid anhydride s-2 of the general formula: 
wherein E34 is as defined above, in a solvent, if necessary, in the presence of an acid.
Amount of acid anhydride s-2: 1 to 5 moles relative to 1 mole of compound a-1
Solvent: organic acids such as acetic acid and propionic acid; aromatic hydrocarbons such as benzene and toluene; etc.
Kind of acid: p-toluenesulfonic acid etc.
Reaction temperature: room temperature to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, D9, V1, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in JP-A 5-25173, or for example, by the following processes.
1) Process of Producing Compound t-1 from Compound a-1
Compound t-1 can be produced from compound a-1 according to the process as described above in Producing Process 2, Step 1).
2) Process of Producing Compound t-2 from Compound t-1
Compound t-2 can be produced by reacting compound t-1 with compound t-3 of the general formula: 
wherein V1 is as defined above, in a solvent in the presence of a base.
Amount of compound t-3: 0.9 to 10 moles relative to 1 mole of compound t-1
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound t-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; and mixtures thereof; etc.
Reaction temperature: xe2x88x9240xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following schemes: 
wherein R1, R2, R3, R4, E35, A, T, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, according to the processes as described in WO98/14452, or for example, by the following processes.
1) Process of Producing Compound u-1 from Compound a-1
Compound u-1 can be produced from compound a-1 according to the process as described above in Producing Process 19, Step 1).
2) Process of producing compound u-2 from Compound u-1
Compound u-2 can be produced by reacting compound u-1 with compound u-12 of the general formula: 
wherein E35 and R215 are as defined above, in a solvent in the presence of a base.
Amount of compound u-12: 0.9 to 10 moles relative to 1 mole of compound u-1
Kind of base: inorganic bases such as sodium hydride, potassium hydroxide, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 0.1 to 10 moles relative to 1 mole of compound u-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N,N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated,. thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound u-3 from Compound u-2
Compound u-3 can be produced by reacting compound u-2 with a methylating agent such as methyl iodide or dimethyl sulfate in a solvent in the presence of a base.
Kind of base: organic bases such as triethylamine; nitrogen-containing compounds such as pyridine; inorganic bases such as sodium hydride, potassium carbonate, and potassium hydroxide; etc.
Amount of base: 1 to 20 moles relative to 1 mole of compound u-2
Amount of methylating agent: 1 to 20 moles relative to 1 mole of compound u-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran; amides such as N,N-dimethylformamide; water; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to room temperature
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound u-4 from Compound u-3
Compound u-4 can be produced by reacting compound u-3 with an oxidizing agent in a solvent.
Kind of oxidizing agent: m-chloroperbenzoic acid, aqueous hydrogen peroxide, etc.
Amount of oxidizing agent: 2 to 20 moles relative to 1 mole of compound u-3
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; halogenated aliphatic hydrocarbons such as chloroform; water; and mixtures thereof; etc.
Reaction temperature: xe2x88x9220xc2x0 C. to room temperature
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
5) Process of Producing Compound u-5 from Compound u-4
Compound u-5 can be produced by reacting compound u-4 with ammonia in a solvent.
Amount of ammonia: 1 mole to large excess relative to 1 mole of compound u-4
Solvent: t-butanol, isopropanol, etc.
Reaction temperature: xe2x88x9220xc2x0 C. to 40xc2x0 C.
Reaction time: a moment to 10 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
6) Process of Producing Compound u-6 from Compound u-4
Compound u-6 can be produced by reacting compound u-4 with an azidizing agent such as sodium azide or trimethylsilyl azide in a solvent such as methanol, ethanol, and water.
Amount of azidizing agent: 1 equivalent to an excess amount relative to 1 mole of compound u-4
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
7) Process of Producing Compound u-7 from Compound u-5
Compound u-7 can be produced by reacting compound u-5 with a haloacetaldehyde such as chloroacetaldehyde (40% aqueous solution) in a solvent.
The amount of haloacetaldehyde is 1 equivalent to an excess amount relative to 1 mole of compound u-5. The solvent may include ethers such as 1,4-dioxane and tetrahydrofuran; water; and mixtures thereof; etc. The reaction temperature is in the range of 40xc2x0 C. to the reflux temperature of the solvent. The reaction time is in the range of a moment to 20 hours.
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining he desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
8) Process of Producing Compound u-8 from Compound u-4
Compound u-8 can be produced by reacting compound u-4 with hydrazine (hydrate) in a solvent or without solvent.
Amount of hydrazine: 1 mole to a large excess amount relative to 1 mole of compound u-4
Solvent: t-butanol, isopropanol, etc.
Reaction temperature: xe2x88x9220xc2x0 C. to 40xc2x0 C.
Reaction time: a moment to 10 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
9) Process of Producing Compound u-9 from Compound u-4
Compound u-9 can be produced by reacting compound u-4 with 2-ethanolamine in a solvent or without solvent.
Amount of 2-ethanolamine: 1 mole to a large excess amount relative to 1 mole of compound u-4
Solvent: t-butanol, isopropanol, etc.
Reaction temperature: xe2x88x9220xc2x0 C. to 40xc2x0 C.
Reaction time: a moment to 10 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
10) Process of Producing Compound u-10 from Compound-u-8
Compound u-10 can be produced by reacting compound u-8 with formic acid in a solvent or without solvent, if necessary, in the presence of another acid.
Kind of acid: p-toluenesulfonic acid, hydrochloric acid, etc.
Amount of acid: 0.001 mole to a large excess amount relative to 1 mole of compound u-8
Amount of formic acid: 1 mole to a large excess amount to 1 mole of compound u-8
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N-N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; alcohols such as methanol and ethanol; water; and mixtures thereof, etc.
Reaction temperature: 40xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 10 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
11) Process of Producing Compound u-11 from Compound u-9
Compound u-11 can be produced by reacting compound u-9 in a solvent or without solvent in the presence of an acid.
Kind of acid: p-toluenesulfonic acid, hydrochloric acid, sulfuric acid, polyphosphoric acid, etc.
Amount of acid: 0.001 mole to a large excess amount relative to 1 mole of compound u-9
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; amides such as N-N-dimethylformamide; ethers such as tetrahydrofuran; halogenated aliphatic hydrocarbons such as chloroform; alcohols such as methanol and ethanol; water; and mixtures thereof; etc.
Reaction temperature: 40xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, R25, E32, E33, E43, T, A, and Y are as defined above; and R216is C1-C6 alkoxy (e.g., methoxy, ethoxy) or NR217(R218 (e.g., dimethylamino, dimethylamino) wherein R217 and R218 are independently C1-C5 alkyl.
The reactions in the respective steps can be carried out, for example, according to the processes as described in Bull. Soc. Chim. Fr. (134, pp. 47-57, 1997), or for example, by the following processes.
1) Process of Producing Compound r-9 from Compound r-6
Compound r-9 can be produced by reacting compound r-6 with compound r-10 of the general formula: 
wherein E33 and R216 are as defined above; R219 and R220 are independently C1-C6 alkyl (e.g., methyl, ethyl), in a solvent, if necessary, in the presence of an acid.
Amount of compound r-10: 1 mole to an excess amount relative to 1 mole of compound r-6
Kind of acid: organic acids such as acetic acid and p-toluenesulfonic acid
Amount of acid: a catalytic amount to large excess relative to 1 mole of compound r-6
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours,
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound r-5 from Compound r-9
Compound r-5 can be produced by reacting compound r-9 with compound a-1 in a solvent, if necessary, in the presence of an acid.
Amount of compound a-1: 0.9 to 1.1 moles relative to 1 mole of compound r-9
Kind of acid: organic acids such as acetic acid and p-toluenesulfonic acid
Amount of acid: a catalytic amount to large excess relative to 1 mole of compound r-9
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Depending upon the kinds of R1, R2, R3, R4, Y, T, and A, the formation of Q may be followed by the introduction or formation of R1, R2, R3, R4, Y, T, and A. In these producing processes, protective groups may be used, if necessary, for the protection, of functional groups from the reactions. (see xe2x80x9cProtective Groups in Organic Synthesisxe2x80x9d written by T. W. Greene.) The following are examples of these producing processes.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, Y11, and Q are as defined above; R221 is methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, aminocarbonyl, or nitrile; and M23 is fluorine, chlorine, or bromine.
The reactions in the respective steps can be carried out, for example, by the following processes.
1) Process of Producing Compound z-2 from Compound z-1
Compound z-2 can be produced by reacting with compound z-1 in a solvent in the presence of a base or acid, and, if necessary, in the presence of a phase transfer catalyst.
Kind of base: inorganic bases such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; etc.
Amount of base: 0.9 to 10 moles relative to 1 mole of compound z-1
Kind of acid: hydrochloric acid, sulfuric acid, etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound z-1
Kind of phase transfer catalyst: tetrabutylammonium bromide etc.
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound z-3 from Compound z-2
Compound z-3 can be produced by heating compound z-2 in a solvent, if necessary, in the presence of an acid or base.
Kind of base: nitrogen-containing compounds such as quinoline and pyridine; amides such as N,N-dimethylformamide; sulfur compounds such as sulforane; aromatic hydrocarbons such as xylene and mesitylene; and mixtures thereof; etc.
Amount of base: 0.9 mole to an excess amount relative to 1 mole of compound z-2
Kind of acid: hydrochloric acid, sulfuric acid, etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound z-2
Kind of phase transfer catalyst: tetrabutylammonium bromide etc.
Solvent: amides such as N,N-dimethylformamide; sulfur compounds such as sulforane; aromatic hydrocarbons such as xylene and mesitylene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; and mixtures thereof; etc.
Reaction temperature: 50xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
In this process, metal catalysts such as copper may be used in their catalytic amounts.
3) Process of Producing Compound z-24 from Compound z-23
Compound z-24 can be produced by reducing compound z-23 with iron powder in a solvent.
Amount of iron powder: 2 to 10 moles relative to 1 mole of compound z-23
Solvent: acetic acid, water, and mixtures thereof, etc.
Reaction temperature: 15xc2x0 C. to 110xc2x0 C.
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound z-25 from Compound z-24
Compound z-25 can be produced by converting compound z-24 into a diazonium salt with sodium nitrite in the presence of an acid and then reacting the diazonium salt with copper halide such as copper (I) chloride or copper (I) bromide.
(Diazonium salt formation)
Amount of sodium nitrite: 1 to 2 moles relative to 1 mole of compound z-24
Kind of acid: sulfuric acid, hydrochloric acid, etc.
Amount of acid: 1 mole to 100 moles relative to 1 mole of compound z-24
Solvent: water, ethanol, hydrochloric acid, etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 24 hours
(Reaction with copper halide)
Kind of copper halide: copper (C) chloride, copper (I) bromide, etc.
Amount of copper halide: 1 to 10 moles relative to 1 mole of compound z-24
Solvent: hydrochloric acid, hydrobromic acid, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 80xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
5) Process of Producing Compound z-3 from Compound z-24
Compound z-3 can be produced by converting compound z-24 into a diazonium salt with sodium nitrite in the presence of an acid and then reacting the diazonium salt in a solvent.
(Diazonium salt formation)
Amount of sodium nitrite: 1 to 2 moles relative to 1 mole of compound z-24
Kind of acid: sulfuric acid, hydrochloric acid, etc.
Amount of acid: 1 mole to 100 moles relative to 1 mole of compound z-24
Solvent: water, ethanol, hydrochloric acid, etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 24 hours
(Thermal decomposition).
Solvent: sulfuric acid, water, etc.
Reaction temperature: room temperature to 200xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R3, R4, R11, Q, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, by the following processes.
1) Process of Producing Compound z-5 from Compound z-4
Compound z-5 can be produced by demethylating compound z-4 in a solvent in the presence of an acid or trimethylsilane iodide.
Kind of acid: inorganic acids such as hydrochloric acid and sulfuric acid; Lewis acids such as boron tribromide and aluminum chloride; etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound z-4
Amount of trimethylsilane iodide: 1 mole to an excess amount relative to 1 mole of compound z-4
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as chloroform; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 168 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound z-6 from Compound z-5
Compound z-6 can be produced by reacting compound z-5 with compound z-18 of the general formula:
M9xe2x80x94R11xe2x80x83xe2x80x83z-18
wherein M9 and R11 are as defined above, in a solvent in the presence of a base.
Amount of compound z-18: 1 to 2 moles relative to 1 mole of compound z-5
Kind of base: potassium carbonate, sodium hydride, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound z-5
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as chloroform; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 100xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R4, Q, T, A, and Y are as defined above; R222 is xe2x80x94OR11 or xe2x80x94SR12 wherein R11 and R12 are as defined above; and R223 is xe2x80x94OR224 or xe2x80x94SR225 wherein R224 and R225 are the same or different and independently hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl; C3-C10 alkynyl, C1-C5 alkoxy C1-C5 allkyl, C1-C5 alkylthio C1-C5 alkyl, or optionally substituted phenyl.
The reactions in the respective steps can be carried out, for example, by the following processes.
1) Process of Producing Compound z-8 from Compound z-7
Compound z-8 can be produced by reacting compound z-19 of the general formula:
Hxe2x80x94R222xe2x80x83xe2x80x83z-19
wherein R222 is as defined above, in a solvent in the presence of a base.
Amount of compound z-19: 1 to 5 moles relative to 1 mole of compound z-7
Kind of base: organic bases such as triethylamine, inorganic bases such as potassium carbonate and sodium hydride; alkoxides such as sodium methoxide and sodium thiomethoxide; etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound z-7
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as chloroform; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof, etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours;
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound z-8 wherein R222 is xe2x80x94OR224 or xe2x80x94SR225; and R224 and R224 are as defined above (hereinafter referred to as compound z-8xe2x80x2) can be used to produce compound z-9 or compound z-10 as shown in the following processes.
2) Process of Producing Compound z-9 from Compound z-8xe2x80x2
Compound z-9 can be produced by reducing compound z-8xe2x80x2 with iron powder in a solvent.
Amount of iron powder: 2 to 10 moles relative to 1 mole of compound z-8xe2x80x2
Solvent: acetic acid, water, and mixtures thereof; etc.
Reaction temperature: 15xc2x0 C. to 110xc2x0 C.
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound z-10 from Compound z-9
Compound z-10 can be produced by converting compound z-9 into a diazonium salt with sodium nitrite in the presence of an acid and then reacting the diazonium salt with a chloride such as copper (I) chloride.
(Diazonium salt formation)
Amount of sodium nitrite: 1 to 2 moles relative to 1 mole of compound z-9
Kind of acid: hydrochloric acid, etc.
Amount of acid: 1 mole to 100 moles relative to 1 mole of compound z-9
Solvent: water, ethanol, hydrochloric acid, etc.
Reaction temperature: xe2x88x9215xc2x0 C. to room temperature
Reaction time: a moment to 24 hours
(Reaction with chloride)
Kind of chloride: copper (a) chloride etc.
Amount of chloride: 1 to 10 moles relative to 1 mole of compound z-9
Solvent: hydrochloric acid etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 80xc2x0 C.
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following process: 
wherein R1, R3, R4, R14, R17, R19, Q, T, A, and Y are as defined above.
The reactions in the respective steps can be carried out, for example, by the following processes.
1) Process of Producing Compound z-12 from Compound z-11
Compound z-12 can be produced by reacting compound z-11 with copper (I) cyanide in a solvent.
Amount of copper (I) cyanide: 1 to 4 moles relative to 1 mole of compound z-11
Kind of solvent: amides such as N,N-dimethylformamide and N-methylpyrrolidone; sulfur compound such as dimethylsulfoxide; etc.
Reaction temperature: 40xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound z-13 from Compound z-12
Compound z-13 can be produced by reacting compound z-12 with water in the presence of an acid.
Amount of water: 1 mole to an excess amount relative to 1 mole of compound z-12
Kind of acid: hydrochloric acid, sulfuric acid, etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound z-12
Reaction temperature: 10xc2x0 C. to 50xc2x0 C.
Reaction time: a moment to 24 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound z-14 from Compound z-13
Compound z-14 can be produced by reacting compound z-13 with water in the presence of an acid or base.
Amount of water: 1 equivalent to an excess amount relative to 1 mole of compound z-13
Kind of acid: hydrochloric acid, sulfuric acid, etc.
Amount of acid: 1 equivalent to an excess amount relative to 1 mole of compound z-13
Kind of base: sodium hydroxide, potassium hydroxide, etc.
Amount of base: 1 to 3 equivalents relative to 1 mole of compound z-13
Reaction temperature: room temperature to 150xc2x0 C.
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound z-17 from Compound z-14
Compound z-17 can be produced by reacting compound z-14 with thionyl chloride to form an acid chloride compound (reaction 1) and then reacting the acid chloride compound with compound z-20 of the general formula:
HOxe2x80x94R14xe2x80x83xe2x80x83z-20
wherein R14 is as defined above, in a solvent in the presence of a base (reaction 2).
(Reaction 1)
Amount of thionyl chloride: 1 mole to an excess amount relative to compound z-14
Reaction temperature: 40xc2x0 C. to the reflux temperature of thionyl chloride
Reaction time: a moment to 10 hours
After completion of the reaction, the reaction mixture was concentrated and used as the starting material for reaction 2.
(Reaction 2)
Amount of compound z-20: 1 mole to an excess amount relative to 1 mole of compound z-14
Kind of base: pyridine, triethylamine, potassium carbonate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound z-14
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as chloroform; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
5) Process of Producing Compound z-17 from Compound z-13
Compound z-17 can be produced by reacting compound z-13 with compound z-20 of the general formula:
HOxe2x80x94R14xe2x80x83xe2x80x83z-20
wherein R14 is as defined above, in a solvent in the presence of a boron trihalide compound.
Amount of compound z-20: 1 mole to an excess amount relative to 1 mole of compound z-13
Kind of boron trihaihde compound: boron trifluoride, boron trichloride, boron tribromide, etc.
Amount of boron trihalide compound: 1 mole to an excess amount relative to 1 mole of compound z-13
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 50xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
6) Process of Producing Compound z-15 from Compound z-12
Compound z-15 can be produced by reacting compound z-12 with compound z-2 1 of the general formula:
M11xe2x80x94Mgxe2x80x94R17xe2x80x83xe2x80x83z-21
wherein R17 is as defined above and M11 is chlorine or bromine, in a solvent.
Amount of compound z-21: 1 to 1.3 moles relative to 1 mole of compound z-12
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as chloroform; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
7) Process of Producing Compound z-16 from Compound z-15
Compound z-16 can be produced by reacting compound z-15 with compound z-22 of the general formula:
R19ONH2xe2x80x83xe2x80x83z-22
wherein R19 is as defined above, in a solvent, if necessary, in the presence of a base.
Amount of compound z-22: 1 to 3 moles relative to 1 mole of compound z-15
Kind of base: triethylamine, pyridine, potassium carbonate, etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound z-15
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
In addition to the above processes, the present compounds can also be produced by making reference to, for example, JP-A 5-213970, EP 683160-A1, and JP-A 61-161288.
The processes of producing some of the starting materials used in the production of the present compounds are explained below.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, and Y11 are as defined above; and R250 is carboxy, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, or nitrile.
The reactions in the respective steps can be carried out, for example, according to the processes as described in Indian Journal of Chemistry. (vol. 20B, pp. 391-393, 1981), Indian Journal of Chemistry (vol. 14B, pp. 6886-6891, 1981), Organic Syntheses (vol. 33, p. 43, 1953), or for example, by the following processes.
1) Process of Producing Compound v-2 from Compound v-1
Compound v-2 can be produced by reacting compound v-1 with compound v-19 of the general formula: 
wherein R250 is as defined above and M20 is chlorine, bromine, or iodine, in a solvent in the presence of a base.
Kind of base: inorganic bases such as potassium carbonate, sodium hydride, and sodium hydroxide; organic bases such as triethylamine; nitrogen-containing compounds such as pyridine; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound v-1
Amount of compound v-19: 0.9 to 3 moles relative to 1 mole of compound v-1
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ketones such as acetone; ethers such as tetrahydrofuran; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof, etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound v-3 from Compound v-2
Compound v-3 can be produced by reacting compound v-2 in a solvent in the presence of a base.
Kind of base: inorganic bases such as potassium carbonate, sodium hydride, and sodium hydroxide; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound v-2
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound v-4 from Compound v-3
Compound v-4 can be produced by reacting compound v-3 in a solvent in the presence of a base or acid and, if necessary, in the presence of a phase transfer catalyst.
Kind of base: inorganic bases such as sodium hydroxide and potassium hydroxide; etc.
Amount of base: 0.9 to 10 moles relative to 1 mole of compound v-3
Kind of acid: hydrochloric acid, sulfuric acid, etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound v-3
Kind of phase transfer catalyst: tetrabutylammonium bromide etc.
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; water; and mixtures thereof; etc.
Reaction temperature: 10xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
4) Process of Producing Compound v-5 from Compound v-4
Compound v-5 can be produced by heating compound v-4 in a solvent, if necessary, in the presence of a base or acid.
Kind of base: nitrogen-containing compounds such as quinoline and pyridine; amides such as N,N-dimethylformamide; sulfur compounds such as sulforane; aromatic hydrocarbons such as xylene and mesitylene; and mixtures thereof; etc.
Amount of base: 0.9 mole to an excess amount relative to 1 mole of compound v-4
Kind of acid: hydrochloric acid, sulfuric acid, etc.
Amount of acid: 1 mole to an excess amount relative to 1 mole of compound v-4
Solvent: amides such as N,N-dimethylformamide; sulfur compounds such as sulforane; aromatic hydrocarbons such as xylene and mesitylene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran and 1,4-dioxane; and mixtures thereof, etc.
Reaction temperature: 50xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 96 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
In this process, metal catalysts such as copper may be used.
Compound v-1 as the starting material in this producing process can also be produced from the corresponding benzaldehyde derivative by making reference to, for example, Shin Jikken Kagaku Koza (published by Maruzen Kabushiki Kaisha) vol. 14, pp. 1466-1470. The benzaldehyde derivative to be used as the starting material at that time can also be produced by making reference to, for example, EP 0312338-A1, Synthetic Communication, 24(12), pp. 1757-1760 (1994), and J. Chem. Soc. Perkin I, pp. 318-321 (1978).
Compound v-2 as the intermediate can also be produced according to the following scheme 1 or 2. 
wherein R1, R2, R3, R4, R250, and Y11 are as defined above; and M21 is fluorine, chlorine, or bromine.
5) Process of Producing Compound v-2 from Compound v-6
Compound v-2 can be produced by reacting compound v-6 with compound v-17 of the formula: 
wherein Y11 and R250 are as defined above, in a solvent in the presence of a base.
Kind of base: inorganic bases such as potassium carbonate, sodium hydride, sodium hydroxide, and potassium fluoride; organic bases such as triethylamine; nitrogen-containing compounds such as pyridine; etc.
Amount of base: 1 to 10 moles relative to 1 mole of compound v-6
Amount of compound v-17: 0.9 to 10 moles relative to 1 mole of compound v-6
Solvent: aromatic hydrocarbons such as benzene and toluene; halo-genated aromatic hydrocarbons such as chlorobenzene; ketones such as acetone; ethers such as tetrahydrofuran and 1,4-dioxane; amides such as N,N-dimethylformamide; and mixtures thereof; etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 72 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography. 
wherein R1, R2, R3, R4, R250, and Y11 are as defined above.
1) Process of Producing Compound v-2 from Compound v-16
Compound v-2 can be produced by reacting compound v-16 with copper (I) cyanide in a solvent.
Amount of copper (I) cyanide: 1 to 4 moles relative to 1 mole of compound v-16
Kind of solvent: amides such as N,N-dimethylformamide and N-methylpyrrolidone; sulfur compound such as dimethylsulfoxide; etc.
Reaction temperature: 40xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 120 hours
After completion of the reaction, ammonia water is added, if necessary, to the reaction mixture, which is then extracted with an organic solvent, and the organic layer is dried and concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, 2, R3, and R4 are as defined above; and M22 is fluorine or chlorine.
The reactions in the respective steps can be carried out, for example, according to the processes as described in Tetrahedron Letters (vol. 37, No. 17, pp. 2885-2886, 1996), or for example, by the following processes.
1) Process of Producing Compound v-8 from Compound v-7
Compound v-8 can be produced by reacting compound v-7 with aceto-hydroxamic acid in a solvent in the presence of a base.
Amount of hydroxamic acid: 1 to 3 moles relative to 1 mole of compound v-7
Kind of base: potassium t-butoxide, sodium hydride, etc.
Amount of base: 1 to 3 moles relative to 1 mole of compound v-7
Solvent: N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, etc.
Reaction temperature: room temperature to 100xc2x0 C.
Reaction time a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, and R4 are as defined above; Y1 is oxygen, sulfur, or N-R142; and R142 is as defined above.
The reactions in the respective steps can be carried out, for example, by the following processes.
1) Process of Producing Compound v-10 from Compound v-9
Compound v-10 can be produced by reacting compound v-9 with a nitrating agent in a solvent or without solvent.
Kind of nitrating agent: nitric acid etc.
Amount of nitrating agent: 1 to 1.5 moles relative to 1 mole of compound v-9
Solvent: acetic anhydride etc.
Reaction temperature: xe2x88x9210xc2x0 C. to 50xc2x0 C.
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound v-11 from Compound v-10
Compound v-11 can be produced by reducing compound v-10 with iron powder in a solvent.
Amount of iron powder: 1 to 10 moles relative to 1 mole of compound v-10
Solvent: acetic acid, water, and mixtures thereof, etc.
Reaction temperature: 15xc2x0 C. to 110xc2x0 C.
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R226 is C1-C10 alkyl and M12 is fluorine or chlorine.
The reactions in the respective steps can be carried out, for example, according to the processes as described in Khim. Geterotsikl. Soedin (1990, Issue 5, pp. 597-600), Khim. Geterotsikl. Soedin (1989, Issue 5, pp. 704), or for example, by the following processes.
1) Process of Producing Compound v-13 from Compound v-12
Compound v-13 can be produced by reacting compound v-12 with nitroenamine compound v-18 of the formula: 
in a solvent and, if necessary, in the presence of an acid.
Amount of compound v-18: 1 to 3.0 moles relative to 1 mole of compound v-12
Kind of acid: acetic acid, p-toluenesulfonic acid, sulfuric acid, etc.
Amount of acid: a catalytic amount to a large excess amount relative to 1 mole of compound v-12
Solvent: aromatic hydrocarbons such as toluene and xylene; ethers such as tetrahydrofuran; organic acids such as acetic acid and propionic acid; amides such as N,N-dimethylformamide; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
2) Process of Producing Compound v-14 from Compound v-13
Compound v-14 can be produced by reacting compound v-13 with an alkylcarbonylating agent in a solvent and, if necessary, in the presence of an acid and a base.
Kind of alkylcarbonylating agent: acetic anhydride, acetyl chloride, etc.
Amount of alkylcarbonylating agent: 1 to 2.0 moles relative to 1 mole of compound v-13
Kind of acid: acetic acid, p-toluenesulfonic acid, sulfuric acid, etc.
Amount of acid: a catalytic amount to a large excess amount relative to 1 mole of compound v-13
Kind of base: sodium hydroxide, potassium carbonate, triethylamine, etc.
Amount of base: a catalytic amount to a large excess amount relative to 1 mole of compound v-13
Solvent: aromatic hydrocarbons such as toluene and xylene; ethers such as tetrahydrofuran; organic acids such as acetic acid and propionic add; inorganic acids such as sulfuric acid; amides such as N,N-dimethylformamide; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
3) Process of Producing Compound v-15 from Compound v-14
Compound v-15 can be produced by reducing compound v-14 with iron powder in a solvent.
Amount of iron powder: 1 to 10 moles relative to 1 mole of compound v-14
Solvent: acetic acid, water, and mixtures thereof, etc.
Reaction temperature: 15xc2x0 C. to 110xc2x0 C.
Reaction time: a moment to 100 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, and A are as defined above; Y2 is nitrogen or Cxe2x80x94R152; and R152 is as defined above.
The reaction can be carried out, for example, according to the processes as described in Synthesis (Issue 1, pp. 1-17, 1977), J. Med. Chem. (Vol. 39, pp. 570-581, 1996), or for example, by the following process.
1) Process of Producing Compound x-3 from Compound x-5
Compound x-3 can be produced by reacting compound x-5 with an aminating agent in a solvent in the presence of a base.
Kind of base: inorganic bases such as potassium carbonate, sodium hydride, sodium hydroxide, and potassium hydroxide; etc.
Amount of base: 1 to 20 moles relative to 1 mole to compound x-5
Kind of aminating agent: hydroxylamine=O-sulfonic acid, chloramine, O-(2,4-dinitrophenyl)hydroxylamine, etc.
Amount of aminating agent: 0.9 to 5 moles relative to 1 mole of compound x-5
Solvent: aromatic hydrocarbons such as benzene and toluene; halogenated aromatic hydrocarbons such as chlorobenzene; ethers such as tetrahydrofuran; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; and mixtures thereof; etc.
Reaction temperature: xe2x88x9210xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
Compound x-5 used as the intermediate in the above reaction can be produced, for example, according to the processes as described in JP-A 7-508259, JP-A 7-508500, WO93/18008, and WO94/25446.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, and Y11 are as defined above.
The reaction can be carried out, for example, according to the process as described in Chem. Pharm. Bull. 32(11), pp. 4260-4270 (1984), or for example, by the following scheme:
1) Process of Producing Compound v-20 from Compound v-1
Compound v-20 can be produced by reacting compound v-1 with bromonitromethane in a solvent in the presence of a base.
Kind of base: inorganic bases such as potassium carbonate, sodium hydride, and sodium hydroxide; organic bases such as triethylamine; nitrogen-containing compounds such as pyridine; metal alcoholates such as sodium methylate and sodium ethylate; etc.
Amount of base: 1 to 5 moles relative to 1 mole of compound v-1
Amount of bromonitromethane: 0.9 to 3 moles realtive to 1 mole of compound v-1
Solvent: aromatic hydrocarbons such as benzene and toluene;
halogenated aromatic hydrocarbons such as chlorobenzene; ketones such as acetone; ethers such as tetrahydrofuran; amides such as N,N-dimethylformamide; alcohols such as methanol, ethanol, and isopropanol; and mixtures thereof, etc.
Reaction temperature: 0xc2x0 C. to the reflux temperature of the solvent
Reaction time: a moment to 48 hours
After completion of the reaction, the reaction mixture is subjected to post-treatments, for example, the reaction mixture is poured into water, and the deposited crystals are collected by filtration and dried; or the reaction mixture is extracted with an organic solvent, and the organic layer was dried and concentrated; or the reaction mixture is concentrated, thereby obtaining the desired compound. The compound can be purified by a technique such as recrystallization or column chromatography.
This is the producing process according to the following scheme: 
wherein R1, R2, R3, R4, R221, Y11, and Q are as defined above.
The reactions in the respective steps can be carried out according to the processes as described in Producing Processes 1 to 23.
The benzonitrile derivatives used in Reference Producing Processes 1 and 2 can be produced from the corresponding benzaldehyde derivatives or benzamide derivatives. (see Shin Jikken Kagaku Koza, edited by Nihon Kagaku Kai, Maruzen Kabushiki Kaisha, 14, pp. 1466-1474)
Examples of the present compounds which can be prepared according to the above producing process are illustrated below; however, the present invention is not limited to these examples.
In the examples, Me indicates methyl; Et, ethyl; Pr, propyl; Bu, butyl; Pen, pentyl; Hex, hexyl; Hep, heptyl; Oct, octyl; i-, iso-; s-, sec-; c-, cyclo-; and groups not particularly indicated are in normal form.
Compounds of the general formulas: 
wherein
A""s are selected from nitrogen or CH;
Y1""s are selected from oxygen or sulfur;
Y2""s are selected from nitrogen or CH,
R2""s are selected from hydrogen, fluorine, chlorine, bromine, iodine, CH2OH, CHO, COOH, CONH2, COCl, SO2Cl, COGH3; SH, OH, NH2, NO2, CN, CH3, CH2Br, CHB2, CBr3, CH2F, CHF2, CF3, O-Me, O-Et, O-Pr, O-i-Pr, O-Bu, O-i-Bu, O-s-Bu, O-Pen, O-c-Pen, O-Hex, O-c-Hex, O-Hep, O-Oct, OCH2CH2F, OCH2CH2Cl, OCH2CH2Br, OCH2CF3, OCH2OCH3, OCH2CH2OCH3, OCH2CH2OCH2CH3, OCH2SCH3, OCH2CH2SCH3, OCH2CH2SCH2CH3, OCH2CHxe2x95x90CH2, OCH(CH3)CHxe2x95x90CH2, OC(CH3)2CHxe2x95x90CH2, OCH2C(Cl)xe2x95x90CH2, OCH(CH3)C(Cl)xe2x95x90CH2, OCH2C(CH3)xe2x95x90CH2, OCH2Cxe2x89xa1CH, OCH(CH3)Cxe2x89xa1CH, OC(CH3)2Cxe2x89xa1CH, OCH2-c-Pr, OCH2-c-Pen, OCH2-c-Hex, OCH2CN, OCH(CH3)CN, OCOMe, OCOEt, OCOPr, OCO-i-Pr, OCOCF3, OCOCF2H, OCH2COOH, OCH2COOMe, OCH2COOEt, OCH2GOOPr, OCH2COO-i-Pr, OCH2COOBu, OCH2COO-s-Bu, OCH2COOPen, OCH2COOHex, OCH2COOHep, OCH2COO-c-Pen, OCH2COO-c-Hex, OCH2COOCH2CHxe2x95x90CH2, OCH2COOCH2Cxe2x89xa1OCH, OCH2COOPh, OCH2COOCH2Ph, OCH2C(xe2x95x90NOMe)COOMe, OCH2C(xe2x95x90NOMe)COOEt, OCH2C(xe2x95x90NOMe)COOPr, OCH2COOCH2COOH, OCH2COOCH2COOMe, OCH2COOCH2COOEt, OCH2COOCH2COOPr, OCH2COOCH2COO-i-Pr, OCH2COOCH2COOBu, OCH2COOCH2COO-c-Pen, OCH2COOCH2COO-c-Hex, OCH2COOCH2COOCH2CHxe2x95x90CH2, OCH2COOCH2COOCH2Cxe2x89xa1CH, OCH2COOCH(CH3)COOH, OCH2COOCH(CH3)COOMe, OCH2COOCH(CH3)COOEt, OCH2COOCH(CH3)COOPr, OCH2COOCH(CH3)COO-i-Pr, OCH2COOCH(CH3)COOBu, OCH2COOCH(CH3)COO-c-Pen, OCH2COOCH(CH3)COO-c-Hex, OCH2COOCH(CH3)COOCH2CHxe2x95x90CH2, OCH2COOCH(CH3)COOCH2Cxe2x89xa1CH, OCH2COOC(CH3)2COOH, OCH2COOC(CH3)2COOMe, OCH2COOC(CH3)2COOEt, OCH2COOC(CH3)2COOPr, OCH2COOC(CH3)2COO-i-Pr, OCH2COOC(CH3)2COOBu, OOH2COOC(CH3)2COO-c-Pen, OCH2COOC(CH3)2COO-c-Hex, OCH2COOC(CH3)2COOCH2CHxe2x95x90CH2, OCH2COOC(CH3)2COOCH2Cxe2x89xa1CH, OCH(CH3)COOH, OCH(CH3)COOMe, OCH(CH3)COOEt, OCH(CH3)COOPr, OCH(CH3)COO-i-Pr, OCH(CH3)COOBu, OCH(CH3)COO-s-Bu, OCH(CH3)COOPen, OCH(CH3)COOHex, OCH(CH3)COOHep, OCH(CH3)COO-c-Pen, OCH(CH3)COO-c-Hex, OCH(CH3)COOCH2CHxe2x95x90CH2, OCH(CH3)COOCH2Cxe2x89xa1CH, OCH(CH3)COOPh, OCH(CH3)COOCH2Ph, OCH(CH3)C(xe2x95x90NOMe)COOMe, OCH(CH3)C(xe2x95x90NOMe)COOEt, OCH(CH3)C(xe2x95x90NOMe)COOPr, OCH(CH3)COOCH2COOH, OCH(CH3)COOCH2COOMe, OCH(CH3)COOCH2COOEt, OCH(CH3)COOCH2COOPr, OCH(CH3)COOCH2COO-i-Pr, OCH(CH3)COOCH2COOBu, OCH(CH3)COOCH2COO-c-Pen, OCH(CH3)COOCH2COO-c-Hex, OCH(CH3)COOCH2COOCH2CHxe2x95x90CH2, OCH(CH3)COOH2COOCH2Cxe2x89xa1CH, OCH(CH3)COOCH(CH3)COOH, OCH(CH3)COOH(CH3)COOMe, OCH(CH3)COOCH(CH3)COOEt, OCH(CH3)COOCH(CH3)COOPr, OCH(CH3)COOCH(CH3)COO-i-Pr, OCH(CH3)COOCH(CH3)COOBu, OCH(CH3)COOCH(CH3)COO-c-Pen, OCH(CH3)COOCH(CH3)COO-c-Hex, OCH(CH3)COOCH(CH3)COOCH2CHxe2x95x90CH2, OCH(CH3)COOCH(CH3)COOCH2Cxe2x89xa1CH, OCH(CH3)COOC(CH3)2COOH, OCH(CH3)COOC(CH3)2COOMe, OCH(CH3)COOC(CH3)2COOEt, OCH(CH3)COOC(CH3)2COOPr, OCH(CH3)COOC(CH3)2COO-i-Pr, OCH(CH3)COOC(CH3)2COOBu, OCH(CH3)COOC(CH3)2COO-c-Pen, OCH(CH3)COOC(CH3)2COO-c-Hex, OCH(CH3)COOC(CH3)2COOCH2CHxe2x95x90CH2, OCH(CH3)COOC(CH3)2COOCH2Cxe2x89xa1CH, OCH2CON(Me)2, OCH2CON(Et)2, OCH(CH3)CON(Me)2, OCH(CH3)CON(Et)2, S-Me, S-Et, S-Pr, S-i-Pr, S-Bu, S-i-Bu, S-s-Bu, S-Pen, S-c-Pen, S-Hex, S-c-Hex, S-Hep, S-Oct, SCH2CH2F, SCH2CH2Cl, SCH2CH2Br, SCH2CF3, SCH2OCH3, SCH2CH2OCH3, SCH2CH2OCH2CH3, SCH2SCH3, SCH2CH2SCH3, SCH2CH2SCH2CH3, SCH2CHxe2x95x90CH2, SCH(CH3)CHxe2x95x90CH2, SC(CH3)2CHxe2x95x90CH2, SCH2C(Cl)CH2, SCH(CH3)C(Cl)xe2x95x90CH2, SCH2C(CH3)xe2x95x90CH2, SCH2Cxe2x89xa1CH, SCH(CH3)Cxe2x89xa1CH, SC(CH3)2Cxe2x89xa1CH, SCH2-c-Pr, SCH2-c-Pen, SCH2-c-Hex, SCH2CN, SCH(CH3)CN, SCOMe, SCOEt, SCOPr, SCO-i-Pr, SCOCF3, SCOCF2H, SCH2COOH, SCH2COOMe, SCH2COOEt, SCH2COOPr, SCH2COO-i-Pr, SCH2COOBu, SCH2COO-s-Bu, SCH2COOPen, SCH2COOHex, SCH2COOHep, SCH2COO-c-Pen, SCH2COO-c-Hex, SCH2COOCH2CHxe2x95x90CH2, SCH2COOCH2Cxe2x89xa1CH, SCH2COOPh, SCH2COOCH2Ph, SCH2COOCH2COOH, SCH2COOCH2COOMe, SCH2COOCH2COOEt, SCH2COOCH2COOPr, SCH2COOCH2COO-i-Pr, SCH2COOCH2COOBu, SCH2COOCH2COO-c-Pen, SCH2COOCH2COO-c-Hex, SCH2COOCH2COOCH2CHxe2x95x90CH2, SCH2COOCH2COOCH2Cxe2x89xa1CH, SCH2COOCH(CH3)COOH, SCH2COOCH(CH3)COOMe, SCH2COOCH(CHOCOOEt, SCH2COOCH(CH3)COOPr, SCH2COOCH(CH3)COO-i-Pr, SCH2COOCH(CH3)COOBu, SCH2COOCH(CH3)COO-c-Pen, SCH2COOH(CH3)COO-c-Hex, SCH2COOCH(CH3)COOCH2CHxe2x95x90CH2, SCH2COOH(CH3)COOCH2Cxe2x89xa1CH, SCH2COOC(CH3)2COOH, SCH2COOC(CH3)2COOMe, SCH2COOC(CH3)2COOEt, SCH2COOC(CH3)2COOPr, SCH2COOC(CH3)2COO-i-Pr, SCH2COOC(CH3)2COOBu, SCH2COOC(CH3)2COO-c-Pen, SCH2COOC(CH3)2COO-c-Hex, SCH2COOC(CH3)2COOCH2CHxe2x95x90CH2, SCH2COOC(CH3)2COOCH2Cxe2x89xa1CH, SCH(CH3)COOH, SCH(CH3)COOMe, SCH(CH3)COOEt, SCH(CH3)COOPr, SCH(CH3)COO-i-Pr, SCH(CH3)COOBu, SCH(CH3)COO-s-Bu, SCH(CH3)COOPen, SCH(CH3)COOHex, SCH(CH3)COOHep, SCH(CH3)COO-c-Pen, SCH(CH3)COO-c-Hex, SCH(CH3)COOCH2CHxe2x95x90CH2, SCH(CH3)COOCH2Cxe2x89xa1CH, SCH(CH3)COOPh, SCH(CH3)COOCH2Ph, SCH(CH3)COOCH2COOH, SCH(CH3)COOCH2COOMe, SCH(CH3)COOCH2COOEt, SCH(CH3)COOCH2COOPr, SCH(CH3)COOCH2COO-i-Pr, SCH(CH3)COOCH2COOBu, SCH(CH3)COOCH2COO-c-Pen, SCH(CH3)COOCH2COO-c-Hex, SCH(CH3)COOCH2COOCH2CHxe2x95x90CH2, SCH(CH3)COOCH2COOCH2Cxe2x89xa1CH, SCH(CH3)COOCH(CH3)COOH, SCH(CH3)COOCH(CH3)COOMe, SCH(CH3)COOCH(CH3)COOEt, SCH(CH3)COOCH(CH3)COOPr, SCH(CH3)COOCH(CH3)COO-i-Pr, SCH(CH3)COOCH(CH3)COOBu, SCH(CH3)COOCH(CH3)COO-c-Pen, SCH(CH3)COOCH(CH3)COO-c-Hex, SCH(CH3)COOCH(CH3)COOCH2CHxe2x95x90CH2, SCH(CH3)COOCH(CH3)COOCH2Cxe2x89xa1CH, SCH(CH3)COOC(CH3)2COOH, SCH(CH3)COOC(CH3)2COOMe, SCH(CH3)COOC(CH3)2COOEt, SCH(CH3)COOC(CH3)2COOPr, SCH(CH3)COOC(CH3)2COO-i-Pr, SCH(CH3)COOC(CH3)2COOBu, SCH(CH3)COOC(CH3)2COO-c-Pen, SCH(CH3)COOC(CH3)2COO-c-Hex, SCH(CH3)COOC(CH3)2COOCH2CHxe2x95x90CH2, SCH(CH3)COOC(CH3)2COOCH2Cxe2x89xa1CH, SCH2CON(Me)2, SCH2CON(Et)2, SCH(CH3)CON(Me)2, SCH(CH3)CON(Et)2, NH-Me, NH-Et, NH-Pr, NH-i-Pr, NH-Bu, NH-i-Bu, NH-s-Bu, NH-Pen, NH-c-Pen, NH-Hex, NH-c-Hex, NH-Hep, NH-Oct, NHCH2CHxe2x95x90CH2, NHCH(CH3)CHxe2x95x90CH2, NHC(CH3)2CHxe2x95x90CH2, NHCH2C(Cl)xe2x95x90CH2, NHCH(CH3)C(Cl)xe2x95x90CH2, NHCH2C(CH3)xe2x95x90CH2, NHCH2Cxe2x89xa1CH, NHCH(CH3)Cxe2x89xa1CH, NHC(CH3)2Cxe2x89xa1CH, NHCH2-c-Pr, NHCH2-c-Pen, NHCH2-c-Hex, NHCH2CN, NHCH(CH3)CN, NHCOMe, NHCOEt, NHCOPr, NHCO-i-Pr, NHCOCF3, NHCOCF2H, NHCOOMe, NHCOOEt, NHCOOPr, NHCOO-i-Pr, NHSO2Me, NHSO2Et, NHSO2Pr, NHSO2-i-Pr, NHSO2CH2Cl, NHSO2CF3, NHCH2COOH, NHCH2COOMe, NHCH2COOEt, NHCH2COOPr, NHCH2COO-i-Pr, NHCH2COOBu, NHCH2COO-s-Bu, NHCH2COOPen, NHCH2COOHex, NHCH2COOHep, NHCH2COO-c-Pen, NHCH2COO-c-Hex, NHCH2COOCH2CHxe2x95x90CH2, NHCH2COOCH2Cxe2x89xa1CH, NHCH2COOPh, NHCH2COOCH2Ph, NHCH2COOCH2COOH, NHCH2COOCH2COOMe, NHCH2COOCH2COOEt, NHCH2COOCH2COOPr, NHCH2COOCH2COO-i-Pr, NHCH2COOCH2COOBu, NHCH2COOCH2COO-c-Pen, NHCH2COOCH2COO-c-Hex, NHCH2COOCH2COOCH2CHxe2x95x90CH2, NHCH2COOCH2COOCH2Cxe2x89xa1CH, NHCH2COOCH(CH3)COOH, NHCH2COOCH(CH3)COOMe, NHCH2COOCH(CH3)COOEt, NHCH2COOCH(CH3)COOPr, NHCH2COOCH(CH3)COO-i-Pr, NHCH2COOCH(CH3)COOBu, NHCH2COOCH(CH3)COO-c-Pen, NHCH2COOCH(CH3)COO-c-Hex, NHCH2COOCH(CH3)COOCH2CHxe2x95x90CH2, NHCH2COOCH(CH3)COOCH2Cxe2x89xa1CH, NHCH2COOC(CH3)2COOH, NHCH2COOC(CH3)2COOMe, NHCH2COOC(CH3)2COOEt, NHCH2COOC(CH3)2COOPr, NHCH2COOC(CH3)2COO-i-Pr, NHCH2COOC(CH3)2COOBu, NHCH2COOC(CH3)2COO-c-Pen, NHCH2COOC(CH3)2COO-c-Hex, NHCH2COOC(CH3)2COOCH2CHxe2x95x90CH2, NHCH2COOC(CH3)2COOCH2Cxe2x89xa1CH, NHCH(CH3)COOH, NHCH(CH3)COOMe, NHCH(CH3)COOEt, NHCH(CH3)COOPr, NHCH(CH3)COO-i-Pr, NHCH(CH3)COOBu, NHCH(CH3)COO-s-Bu, NHCH(CH3)COOPen, NHCH(CH3)COOHex, NHCH(CH3)COOHep, NHCH(CH3)COO-c-Pen, NHCH(CH3)COO-c-Hex, NHCH(CH3)COOCH2CHxe2x95x90CH2, NHCH(CH3)COOCH2Cxe2x89xa1CH, NHCH(CH3)COOPh, NHCH(CH3)COOCH2Ph, NHCH(CH3)COOCH2COOH, NHCH(CH3)COOCH2COOMe, NHCH(CH3)COOCH2COOEt, NHCH(CH3)COOCH2COOPr, NHCH(CH3)COOCH2COO-i-Pr, NHCH(CH3)COOCH2COOBu, NHCH(CH3)COOCH2COO-c-Pen, NHCH(CH3)COOCH2COO-c-Hex, NHCH(CH3)COOCH2COOCH2CHxe2x95x90CH2, NHCH(CH3)COOCH2COOCH2Cxe2x89xa1CH, NHCH(CH3)COOCH(CH3)COOH, NHCH(CH3)COOCH(CH3)COOMe, NHCH(CH3)COOCH(CH3)COOEt, NHCH(CH3)COOCH(CH3)COOPr, NHCH(CH3)COOCH(CH3)COO-i-Pr, NHCH(CH3)COOCH(CH3)COOBu, NHCH(CH3)COOCH(CH3)COO-c-Pen, NHCH(CH3)COOCH(CH3)COO-c-Hex, NHCH(CH3)COOCH(CH3)COOCH2CHxe2x95x90CH2, NHCH(CH3)COOCH(CH3)COOCH2Cxe2x89xa1CH, NHCH(CH3)COOC(CH3)2COOH, NHCH(CH3)COOC(CH3)2COOMe, NHCH(CH3)COOC(CH3)2COOEt, NHCH(CH3)COOC(CH3)2COOPr, NHCH(CH3)COOC(CH3)2COO-i-Pr, NHCH(CH3)COOC(CH3)2COOBu, NHCH(CH3)COOC(CH3)2COO-c-Pen, NHCH(CH3)COOC(CH3)2COO-c-Hex, NHCH(CH3)COOC(CH3)2COOCH2CHxe2x95x90CH2, NHCH(CH3)COOC(CH3)2COOCH2Cxe2x89xa1CH, NHCH2CON(Me)2, NHCH2CON(Et)2, NHCH(CH3)CON(Me)2, NHCH(CH3)CON(Et)2, COOH, COOMe, COOEt, COOPr, COO-i-Pr, COOBu, COO-s-Bu, COOPen, COOHex, COOCH2Ph, COO-c-Pen, COO-c-Hex, COOCH2COOH, COOCH2COOMe, COOCH2COOEt, COOCH2COOPr, COOCH2COO-i-Pr, COOCH2COOBu, COOCH2COO-c-Pen, COOCH2COO-c-Hex, COOCH2COOCH2CHxe2x95x90CH2, COOCH2COOCH2Cxe2x89xa1CH, COOCH(CH3)COOH, COOCH(CH3)COOMe, COOCH(CH3)COOEt, COOCH(CH3)COOPr, COOCH(CH3)COO-i-Pr, COOCH(CH3)COOBu, COOCH(CH3)COO-c-Pen, COOCH(CH3)COO-c-Hex, COOCH(CH3)COOCH2CHxe2x95x90CH2, COOCH(CH3)COOCH2Cxe2x89xa1CH, COOC(CH3)2COOH, COOC(CH3)2COOMe, COOC(CH3)2COOEt, COOC(CH3)2COOPr, COOC(CH3)2COO-i-Pr, COOC(CH3)2COOBu, COOC(CH3)2COO-c-Pen, COOC(CH3)2COO-c-Hex, COOC(CH3)2COOCH2CHxe2x95x90CH2, COOC(CH3)2COOCH2Cxe2x89xa1CH, CON(Et)2, CON(Me)2, CON(Et)2, CH2CH2COOH, CH2CH2COOMe, CH2CH2COOEt, CH2CH2COOPr, CH2CH2COO-i-Pr, CH2CH2COOBu, CH2CH(Cl)COOH, CH2CH(Cl)COOMe, CH2CH(Cl)COOEt, CH2CH(Cl)COOPr, CH2CH(Cl)COO-i-Pr, CH2CH(Cl)COOBu, CHxe2x95x90CHCOOH, CHxe2x95x90CHCOOMe, CHxe2x95x90CHCOOEt, CHxe2x95x90CHCOOPr, CHxe2x95x90CHCOO-i-Pr, CHxe2x95x90CHCOOBu, CHxe2x95x90C(Cl)COOH, CHxe2x95x90C(Cl)COOMe, CHxe2x95x90C(Cl)COOEt, CHxe2x95x90C(Cl)COOPr, CHxe2x95x90C(Cl)COO-i-Pr, CHxe2x95x90C(Cl)COOBu, C(Me)xe2x95x90CHCOOH, C(Me)xe2x95x90CHCOOMe, C(Me)xe2x95x90CHCOOEt, C(Me)xe2x95x90CHCOOPr, C(Me)xe2x95x90CHCOO-i-Pr, C(Me)xe2x95x90CHCOOBu, CHxe2x95x90C(Me)COOH, CHxe2x95x90C(Me)COOMe, CHxe2x95x90C(Me)COOEt, CHxe2x95x90C(Me)COOPr, CHxe2x95x90C(Me)COO-i-Pr, CHxe2x95x90C(Me)COOBu, CHxe2x95x90NOH, CHxe2x95x90NOMe, CHxe2x95x90NOEt, CHxe2x95x90NOPr, CHxe2x95x90NO-i-Pr, CHxe2x95x90NOBu, C(Me)xe2x95x90NOH, C(Me)xe2x95x90NOMe, C(Me)xe2x95x90NEt, C(Me)xe2x95x90NOPr, C(Me)xe2x95x90NO-i-Pr, C(Me)xe2x95x90NOBu, CHxe2x95x90NOCH2COOMe, CHxe2x95x90NOCH2COOEt, CHxe2x95x90NOCH2COOPr, CHxe2x95x90NOCH2COO-i-Pr, CHxe2x95x90NOCH2COOBu, C(Me)xe2x95x90NOCH2COOMe, C(Me)xe2x95x90NOCH2COOEt, C(Me)xe2x95x90NOCH2COOPr, C(Me)xe2x95x90NOCH2COO-i-Pr, or (Me)xe2x95x90NOCH2COOBu;
R3xe2x80x2s are selected from hydrogen, fluorine, chlorine, bromine, iodine, NO2, CN, O-Me, O-Et, O-Pr, O-i-Pr, O-Bu, O-i-Bu, O-s-Bu, O-Pen, O-c-Pen, O-Hex, O-c-Hex, O-Hep, O-Oct, OCH2COOMe, OCH2COOEt, OCH2COOPr, OCH2COO-i-Pr, OCH2COOBu, OCH2COO-s-Bu, OCH2COOPen, OCH2COOHex, OCH2COOHep, OCH2C(xe2x95x90NOMe)COOMe, OCH2C(xe2x95x90NOMe)COOEt, OCH2C(xe2x95x90NOMe)COOPr, OCH(CH3)COOMe, OCH(CH3)COOEt, OCH(CH3)COOPr, OCH(CH3)COO-i-Pr, OCH(CH3)COOBu, OCH(CH3)COO-s-Bu, OCH(CH3)COOPen, OCH(CH3)COOHex, OCH(CH3)COOHep, OCH(CH3)C(xe2x95x90NOMe)COOMe, OCH(CH3)C(xe2x95x90NOMe)COOEt, or OCH(CH3)C(xe2x95x90NOMe)COOPr; and
R4xe2x80x2s are selected from hydrogen, fluorine, chlorine, bromine, iodine, NO2, or CN.